CN109134496A - A kind of novel synthesis of natural products (-)-Porantheridine - Google Patents
A kind of novel synthesis of natural products (-)-Porantheridine Download PDFInfo
- Publication number
- CN109134496A CN109134496A CN201811255877.XA CN201811255877A CN109134496A CN 109134496 A CN109134496 A CN 109134496A CN 201811255877 A CN201811255877 A CN 201811255877A CN 109134496 A CN109134496 A CN 109134496A
- Authority
- CN
- China
- Prior art keywords
- under
- room temperature
- porantheridine
- conditions
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/16—Peri-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses the novel synthesis of natural products (-)-Porantheridine a kind of; the present invention is using known 1 compound of formula as starting material; it is protected by tert-butyl carbonyl; MHorner-Wadsworth-Emmons reaction; N-Michael reaction, the Wacker oxidation reaction of Pd (II) catalysis and the series reactions such as ring closure reaction synthesize target molecule.The design of the entire route of the present invention is unique novel, and reaction process reaction condition is mild, and rate is fast, and side reaction is relatively smaller, easy to operate, and what is utilized in route is conventional chemical reagent, and raw material is cheap and easy to get, can substantially reduce synthesis cost.
Description
Technical field
The present invention relates to the synthetic methods of natural products key intermediate, in particular to a kind of natural products (-)-
The novel synthesis of Porantheridine.
Background technique
Tricyclic alkaloid (-)-Porantheridine in 1972 by j.a.Lamberton and colleague from Australia
Bush Poranthera corymbosa in separate.Its absolute configuration determines by X-ray analysis, and by
D.Comins and h.Huong completed determining asymmetric syntheses in 1993.
Alkaloid is due to being always biologist, pharmacy man and organic conjunction with good bioactivity and complicated structure
The target pursued at chemist.Porantheridine alkaloid is a kind of more complicated natural products molecule of structure.Therefore,
After natural products is separated, they become always to people's attractive synthesis target by force.Till now,
Have multiple groups in the world to report to the study on the synthesis of Porantheridine report.
The method of current synthesis of natural product reported in the literature mainly has:
1. (1) Goessinger et al. was published in entitled on Tetrahedron Letters in 1980
The research paper of Stereoselektive synthese von (±)-Porantheridine；(2)Comins,Daniel L.
Et al. entitled Asymmetric on Journal of the American Chemical Society was published in 1993
The research paper of Synthesis of (-)-Porantheridine；(3) David, Marc et al. were published in The in 1999 years
Entitled Efficient total synthesis of enantiopure on Journal of Organic Chemistry
The research paper of (-)-Porantheridine；(4) Takahata, Hiroki et al. were published in Organic and in 2006 years
Entitled A new route to trans-2,6-disubstituted on Biomolecular Chemistry
piperidine-related alkaloids using a novel C2-symmetric 2,6-diallylpiperidine
The research paper of carboxylic acid methyl ester；(5) Bates, Roderick W et al. was published in 2009 years
Entitled A formal synthesis of Porantheridine and on Journal of Organic Chemistry
an epimer；
(6) 2010 years, entitled Synthetic of the Pierre Sancibrao et al. on J.Org.Chem.
Approaches to Racemic Porantheridine and 8-Epihalosaline via a Nitroso Diels-
The research paper of Alder Cycloaddition/Ring-Rearrangement Metathesis Sequence；(7)2013
The entitled Stereodivergent Synthesis of that year Guillaume Vincent et al. delivers on Chem.Eur.J.
Piperidine Alkaloids by Ring-Rearrangement Metathesis/Reductive Lactam
The research paper of Alkylation of Nitroso Diels-Alder Cycloadducts；(8) 2017 years, Roderick
The entitled Synthesis of the sedum and related that W.Bates etc. is delivered on Tetrahedron Letters
The research paper of alkaloids:A personal perspective.
Fully synthetic highway route design and method in the prior art are carefully analyzed, has synthesis step longer or synthesis
The shortcomings that strategy is single, reacts not easy to operate, expensive reagents individually and is more toxic.
Summary of the invention
There are routes present invention aim to overcoming existing synthetic method it is long, synthesis cost is expensive the problems such as, provide
A kind of synthetic method of completely new natural products (-)-Porantheridine.
The present invention is intended to provide a completely new synthetic route, referring to 1 present invention of Figure of description with known 1 compound of formula
It for starting material, is protected by tert-butyl carbonyl, MHorner-Wadsworth-Emmons reaction, N-Michael reaction,
Wacker oxidation reaction and the series reactions such as ring closure reaction synthesize target molecule.The design of the entire route of the present invention is unique
Novelty, reaction process reaction condition is mild, and rate is fast, and side reaction is relatively smaller, easy to operate, and what is utilized in route is conventional
Chemical reagent, raw material is cheap and easy to get, can substantially reduce synthesis cost.
In order to achieve the above object, the new synthesis side of natural products (-)-Porantheridine designed by the present invention
Method, its special feature is that, include the following steps:
A kind of novel synthesis of natural products (-)-Porantheridine, includes the following steps:
1) byIt reacts to obtain with amyl- 4- alkene -1- base magnesium bromide
2) rightTertbutyloxycarbonyl protection reaction is carried out, is obtained
3) -78 DEG C at a temperature of, using methylene chloride as solvent,Also with diisobutyl aluminium hydride
It is 0.5-1 hours former, it obtains；
4)Using tetrahydrofuran as solvent, under the conditions of 0 DEG C, under the action of sodium hydride, withIt reacts to obtain open loop by MHorner-Wadsworth-Emmons
5)At -20 DEG C, solvent is made with methylene chloride, ring closure reaction occurs under the action of TfOH
It obtains
6)Selective reduction is available
7)Under room temperature, oxygen presence and the catalysis of palladium chloride and stannous chloride, with N, N- bis-
Methylformamide: solvent is made in water 10:1 mixing, carries out Wacker oxidation reaction, can obtain
8)At 0 DEG C, under conditions of trifluoroacetic acid, solvent is made with methylene chloride, carries out de- Boc and cyclization
Reaction obtainsBoth (-)-Porantheridine is obtained；
The novel synthesis of described natural products (-)-Porantheridine: in step 1), the condition of reaction are as follows:
Under 0 DEG C and the protection of nitrogen, toTetrahydrofuran solution in be added dropwise methyl-magnesium-bromide, solution becomes white, stirring
It 5 minutes, is warmed to room temperature and is stirred at room temperature 0.5 hour, be cooled to 0 DEG C again, and by amyl- 4- alkene -1- base under the conditions of 0 DEG C
Magnesium bromide is slowly added dropwise into above-mentioned solution, is warmed to room temperature after being stirred to react 12 hours, and sodium cyanoborohydride is added under the conditions of 0 DEG C
And glacial acetic acid is injected, separating-purifying obtains after reacting 45 minutes at room temperature
The novel synthesis of described natural products (-)-Porantheridine: in step 2), tertbutyloxycarbonyl protection
The condition of reaction are as follows: under the protection of room temperature and nitrogen,It is dissolved in tetrahydrofuran solution, 4- is added
Dimethylamino naphthyridine and stir 0.5 hour after, di-tert-butyl dicarbonate is added dropwise under the conditions of 0 DEG C, at room temperature react 18 hours after, warp
Separating-purifying is crossed to obtain
The novel synthesis of described natural products (-)-Porantheridine: in step 3), the condition of carbonyl reduction
Are as follows: under the protection of room temperature and nitrogen,Be dissolved in dichloromethane solution, be then cooled to -78 DEG C and
Under the conditions of this temperature, diisobutyl aluminium hydride is slowly dropped into the solution, and after being reacted 0.5~1 hour at -78 DEG C,
It is obtained by separating-purifying
The novel synthesis of described natural products (-)-Porantheridine: in step 4), in room temperature and nitrogen
Protection under, willIt is dissolved in tetrahydrofuran solution, sodium hydride is added under the conditions of 0 DEG C, stirs at room temperature
After mixing 1 hour, tetrahydrofuran will be dissolved under the conditions of 0 DEG CAfter being slowly dropped in above-mentioned solution, rise
It is stirred to react 2.5 hours to room temperature and at this, separating-purifying obtains
The novel synthesis of described natural products (-)-Porantheridine: in step 5), in room temperature and nitrogen
Protection under, willIt is dissolved in dichloromethane solution, is added dropwise under the conditions of -20 DEG C and is dissolved in methylene chloride
TfOH and after reacting 5 hours under the conditions of the temperature, separating-purifying obtains
The novel synthesis of described natural products (-)-Porantheridine: in step 6), in room temperature and nitrogen
Protection under, willIt is dissolved in methanol, be subsequently cooled to 0 DEG C and sodium borohydride, room temperature condition are added at such a temperature
After lower reaction 1-1.5 hours, separating-purifying is obtained
The novel synthesis of described natural products (-)-Porantheridine:, will in step 7)
Be dissolved in n,N-Dimethylformamide: water is the solution of 10:1, and palladium chloride and stannous chloride is then added, and in room temperature and is full of oxygen
Under conditions of react 24 hours after, filtering, separating-purifying is available
The novel synthesis of described natural products (-)-Porantheridine:, will in step 8)
It is dissolved in dichloromethane solution, is cooled to 0 DEG C and trifluoroacetic acid is slowly added dropwise under the conditions of the temperature, at room temperature instead
After answering 2 hours, separating-purifying is obtainedBoth (-)-Porantheridine is obtained.
Beneficial effects of the present invention:
1, the design of entire synthetic route is unique novel, obtains the synthesis of (-)-Porantheridine single selective, speed
Rate is fast, and side reaction is relatively smaller, and product yield is high；
2, what is utilized in route is conventional chemical reagent, and raw materials and reagents are cheap and easy to get, can be greatly reduced and be produced into
This；
3, synthetic route designs advantages of simple, and operating procedure is easy, and reaction process reaction condition is mild, linear step
It is few, it is suitable for industrially prepared.
Detailed description of the invention
Fig. 1 is the flow chart of reaction of the invention.
Specific embodiment
In order to better explain the present invention, below in conjunction with specific embodiment, the present invention is described in further detail.It answers
Work as understanding, described herein specific examples are only used to explain the present invention, is not intended to limit the present invention.
Embodiment 1
As described in Figure of description 1
1) synthesis of 2 compound of formula:
Under the protection of 0 DEG C and nitrogen, to the tetrahydrofuran (210mL) of 1 compound of formula (5.06g, 44.76mmol)
Methyl-magnesium-bromide (47.4mL) is added dropwise in solution, solution becomes white opacity, restores to stir 30 to room temperature and at room temperature
After minute, it is cooled to 0 DEG C again and amyl- 4- alkene -1- base magnesium bromide (70.6mL) is added dropwise at this temperature, then in room temperature item
After stirring 12 hours under part；The sodium bicarbonate solution (40 mL) of saturation is added into mixed system, with ethyl acetate (3 ×
It 80mL) extracts, merges obtained organic phase, it is dry with saturated common salt water washing and anhydrous sodium sulfate, it is concentrated under reduced pressure and removes
Organic solvent, obtained crude product obtain white liquid after flash chromatography (methanol: methylene chloride=1:60) separating-purifying
Body, i.e. 2 compound of formula (5.32g, 71%).
2) synthesis of 3 compound of formula
Under the protection of room temperature and nitrogen, 2 compound of wushu (2.26g, 13.52mmol) is dissolved in tetrahydrofuran
It in (65mL), is added 4-dimethylaminopyridine (1.65g, 13.52 mmol), after stirring 30 minutes, is added dropwise two under the conditions of 0 DEG C
Dimethyl dicarbonate butyl ester (1.17mL, 5.10mmol).The ammonium chloride solution (20mL) of saturation is added into mixed system, uses acetic acid
Ethyl ester (3 × 80mL) extraction, merges obtained organic phase, and with saturated common salt water washing, anhydrous sodium sulfate dries organic phase, so
Removal organic solvent is concentrated under reduced pressure afterwards and obtains crude product, the crude product then obtained passes through flash chromatography (ethyl acetate: petroleum
Ether=1:9) separating-purifying obtains yellow oily liquid, i.e. 3 compound of formula (3.40g, 94%).
3) synthesis of 4 compound of formula
It is under the protection of room temperature and nitrogen, the methylene chloride (26mL) of 3 compound of formula (0.7g, 2.62mmol) is molten
Liquid is cooled to -78 DEG C, the diisobutyl aluminium hydride (4.4mL) of 1.5M is then slowly added dropwise, and react 0.5 under the conditions of this temperature
~1 hour is then added methanol (5mL) and continues stirring 15 minutes under the conditions of -78 DEG C, it is full that sodium potassium tartrate tetrahydrate is then added
With solution (10mL), rise to room temperature and at room temperature stir 1 hour, obtained mixed system with methylene chloride (3 ×
It 80mL) extracts, merges obtained organic phase, with saturated common salt water washing, anhydrous sodium sulfate is dry, and it is organic that removal is concentrated under reduced pressure
Solvent, obtained crude product obtain colorless oil liquid by flash chromatography (ethyl acetate: petroleum ether=1:10) separating-purifying
Body, i.e. 4 compound of formula ((0.63g, 89%).
4) synthesis of 6 compound of formula
Under the protection of room temperature and nitrogen, 5 compound of wushu (4.3g, 22mmol) is dissolved in tetrahydrofuran (120mL),
It is added under the conditions of 0 DEG C to sodium hydride (0.88g, 22mmol), after stirring 1 hour at room temperature, under the conditions of 0 DEG C, upwards
4 compound of formula (2.96g, 10.99mmol) that addition is dissolved in tetrahydrofuran (30mL) in mixture is stated, is stirred at room temperature anti-
After answering 2.5 hours, the ammonium chloride solution (20 mL) of saturation is added into mixed system, is extracted with methylene chloride (3 × 30mL),
Merge obtained organic phase, with saturated common salt water washing, then it is organic that removal is concentrated under reduced pressure in the dry organic phase of anhydrous sodium sulfate
Solvent obtains crude product, and the crude product then obtained passes through flash chromatography (ethyl acetate: petroleum ether=1:10) separating-purifying
Obtain colourless oil liquid, i.e. 6 compound of formula (3.03g, 82%).
5) synthesis of 7 compound of formula
Under the protection of room temperature and nitrogen, 6 compound of formula (182mg, 0.54mmol) is dissolved in methylene chloride (54mL)
In, -20 DEG C are cooled to, TfOH (0.54mmol, CH is added2Cl2, 0.2M), and after being stirred 5 hours at -20 DEG C, saturation is added
Sodium bicarbonate solution (40mL) quenching reaction.The mixed system obtained after being quenched is extracted with methylene chloride (3 × 80mL), is merged
Obtained organic phase, with saturated common salt water washing, anhydrous sodium sulfate is dry, is then concentrated under reduced pressure and removes organic solvent, obtains
Crude product isolate and purify to obtain 7 compound of colourless liquid formula by flash chromatography (ethyl acetate: petroleum ether=1:30)
(141mg, 78%).
6) synthesis of 8 compound of formula
Under the protection of room temperature and nitrogen, 7 compound of formula (1.42mg, 4.21mmol) is dissolved in methanol solution
In (21mL), it is cooled to 0 DEG C, and sodium borohydride solids (0.57g, 15.16mmol) is added at 0 DEG C, is then stirred at room temperature
After mixing 30 minutes, the ammonium chloride solution (30mL) of saturation is added into mixed system, is extracted with methylene chloride (3 × 30mL), closes
And obtained organic phase, with saturated common salt water washing, then it is organic molten that removal is concentrated under reduced pressure in the dry organic phase of anhydrous sodium sulfate
Agent obtains crude product, and the crude product then obtained is obtained by flash chromatography (ethyl acetate: petroleum ether=1:20) separating-purifying
To colourless oil liquid, i.e. 8 compound of formula (1.11g, 78%).
7) synthesis of 9 compound of formula
Under room temperature and oxygen protective condition, 8 compound of formula (0.85g, 2.50mmol) is dissolved in N, N- dimethyl formyl
In the solution (55mL) of amine/water (10:1), be then added palladium chloride (0.18g, 1.0mmol) and stannous chloride (1.24g,
12.5mmol), after reacting 24 hours under room temperature, diatomite filtering is extracted with methylene chloride (3 × 60mL), merges gained
The organic phase arrived, with saturated common salt water washing, then the dry organic phase of anhydrous sodium sulfate is concentrated under reduced pressure removal organic solvent and obtains
Crude product, the crude product then obtained obtain colourless liquid by flash chromatography (ethyl acetate: petroleum ether=1:3) separating-purifying
Body, i.e. 9 compound of formula (0.74g, 83%).
8) (-)-Porantheridine is synthesized
Under room temperature and oxygen protective condition, 8 compound of modus ponens (62mg, 0.17mmol) is dissolved in dichloromethane solution
In (11mL), trifluoroacetic acid (1.24 mL) is slowly added dropwise under the conditions of 0 DEG C, after stirring 2 hours at room temperature, uses vacuum
Rotary Evaporators take the unstable earnest in mixed system away, and 20mL saturated solution of sodium bicarbonate is added in remaining mixed system,
It is extracted with methylene chloride (3 × 40mL), merges obtained organic phase, filtered first with diatomite, then washed with saturated common salt
It washs, anhydrous sodium sulfate is dry, and removal organic solvent is then concentrated under reduced pressure and obtains crude product, the crude product then obtained is by flash
Column chromatography (methanol: methylene chloride=1:10) separating-purifying obtains colourless liquid, i.e. (-)-Porantheridine ((35mg,
85%).
The foregoing is merely presently preferred embodiments of the present invention, is not intended to limit the invention, it is all in spirit of the invention and
Made any modifications, equivalent replacements, and improvements etc., should all be included in the protection scope of the present invention within principle.
Claims (9)
1. a kind of novel synthesis of natural products (-)-Porantheridine, which comprises the steps of:
1) byIt reacts to obtain with amyl- 4- alkene -1- base magnesium bromide
2) rightTertbutyloxycarbonyl protection reaction is carried out, is obtained
3) -78 DEG C at a temperature of, using methylene chloride as solvent,It is restored with diisobutyl aluminium hydride
It 0.5-1 hours, obtains
4)Using tetrahydrofuran as solvent, under the conditions of 0 DEG C, under the action of sodium hydride, withIt reacts to obtain open loop by MHorner-Wadsworth-Emmons
5)At -20 DEG C, solvent is made with methylene chloride, ring closure reaction occurs under the action of TfOH and obtains
6)Selective reduction is available
7)Under room temperature, oxygen presence and the catalysis of palladium chloride and stannous chloride, with N, N- dimethyl
Formamide: solvent is made in water 10:1 mixing, carries out Wacker oxidation reaction, can obtain
8)At 0 DEG C, under conditions of trifluoroacetic acid, solvent is made with methylene chloride, carries out de- Boc and ring closure reaction
It obtainsBoth (-)-Porantheridine is obtained.
2. the novel synthesis of natural products (-)-Porantheridine according to claim 1, it is characterised in that: step
It is rapid 1) in, the condition of reaction are as follows: under the protection of 0 DEG C and nitrogen, toTetrahydrofuran solution in methyl bromide is added dropwise
Change magnesium, solution becomes white, stirs 5 minutes, is warmed to room temperature and is stirred at room temperature 0.5 hour, be cooled to 0 DEG C again, and 0
Amyl- 4- alkene -1- base magnesium bromide is slowly added dropwise into above-mentioned solution under the conditions of DEG C, is warmed to room temperature after being stirred to react 12 hours, 0 DEG C
Under the conditions of be added and sodium cyanoborohydride and inject glacial acetic acid, separating-purifying obtains after reacting 45 minutes at room temperature
3. the novel synthesis of natural products (-)-Porantheridine according to claim 1, it is characterised in that: step
It is rapid 2) in, the condition of tertbutyloxycarbonyl protection reaction are as follows: under the protection of room temperature and nitrogen,It is dissolved in
In tetrahydrofuran solution, after 4-dimethylaminopyridine is added and stirs 0.5 hour, di-tert-butyl dicarbonate is added dropwise under the conditions of 0 DEG C,
After reacting 18 hours at room temperature, obtained by separating-purifying
4. the novel synthesis of natural products (-)-Porantheridine according to claim 1, it is characterised in that: step
It is rapid 3) in, the condition of carbonyl reduction are as follows: under the protection of room temperature and nitrogen,It is dissolved in dichloromethane solution
In, it is then cooled to -78 DEG C and under the conditions of this temperature, diisobutyl aluminium hydride is slowly dropped into the solution, and -78
After being reacted 0.5~1 hour at DEG C, obtained by separating-purifying
5. the novel synthesis of natural products (-)-Porantheridine according to claim 1, it is characterised in that: step
It is rapid 4) in, under the protection of room temperature and nitrogen, willIt is dissolved in tetrahydrofuran solution, under the conditions of 0 DEG C
Sodium hydride is added, after being stirred at room temperature 1 hour, tetrahydrofuran will be dissolved under the conditions of 0 DEG CSlowly
After being added drop-wise in above-mentioned solution, it is warmed to room temperature and is stirred to react 2.5 hours at this, separating-purifying obtains
6. the novel synthesis of natural products (-)-Porantheridine according to claim 1, it is characterised in that: step
It is rapid 5) in, under the protection of room temperature and nitrogen, willIt is dissolved in dichloromethane solution, in -20 DEG C of conditions
After lower dropwise addition is dissolved in the TfOH of methylene chloride and reacts 5 hours under the conditions of the temperature, separating-purifying is obtained
7. the novel synthesis of natural products (-)-Porantheridine according to claim 1, it is characterised in that: step
It is rapid 6) in, under the protection of room temperature and nitrogen, willIt is dissolved in methanol, is subsequently cooled to 0 DEG C and at such a temperature
Sodium borohydride is added, after reacting 1-1.5 hours under room temperature, separating-purifying is obtained
8. the novel synthesis of natural products (-)-Porantheridine according to claim 1, it is characterised in that: step
It is rapid 7) in, willBe dissolved in n,N-Dimethylformamide: water is the solution of 10:1, and palladium chloride is then added
And stannous chloride, in room temperature and under conditions of be full of oxygen after reaction 24 hours, filtering, separating-purifying is available
9. the novel synthesis of natural products (-)-Porantheridine according to claim 1, it is characterised in that: step
It is rapid 8) in, willIt is dissolved in dichloromethane solution, is cooled to 0 DEG C and is slowly added dropwise three under the conditions of the temperature
Fluoroacetic acid, after reacting 2 hours at room temperature, separating-purifying is obtainedBoth (-)-was obtained
Porantheridine。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811255877.XA CN109134496B (en) | 2018-10-26 | 2018-10-26 | Method for synthesizing natural product (-) -Porantheridine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811255877.XA CN109134496B (en) | 2018-10-26 | 2018-10-26 | Method for synthesizing natural product (-) -Porantheridine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN109134496A true CN109134496A (en) | 2019-01-04 |
| CN109134496B CN109134496B (en) | 2019-12-24 |
Family
ID=64810181
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201811255877.XA Active CN109134496B (en) | 2018-10-26 | 2018-10-26 | Method for synthesizing natural product (-) -Porantheridine |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109134496B (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105294725A (en) * | 2015-11-03 | 2016-02-03 | 江西科技师范大学 | Asymmetric synthesis method for natural products Aculeatins A, B, D and 6-epi-Aculeatin D |
-
2018
- 2018-10-26 CN CN201811255877.XA patent/CN109134496B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105294725A (en) * | 2015-11-03 | 2016-02-03 | 江西科技师范大学 | Asymmetric synthesis method for natural products Aculeatins A, B, D and 6-epi-Aculeatin D |
Non-Patent Citations (8)
Also Published As
| Publication number | Publication date |
|---|---|
| CN109134496B (en) | 2019-12-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Malik et al. | Ruthenium-catalyzed one-pot ring-closing metathesis/syn-dihydroxylation in the synthesis of bicyclic iminosugars | |
| CN107383026B (en) | A kind of synthetic method of 7- methylol -2,5- diaza spiro [3,4] octane -2- t-butyl formate | |
| US11339179B2 (en) | Preparation for natural product trabectedin | |
| CN107522698B (en) | Preparation method and intermediate of trabectedin | |
| CN106892928B (en) | A kind of synthetic method of tertiary butyl -8- hydroxyls -5- oxa- -2- azaspiros [3.5] nonane -2- carboxylates | |
| Cogswell et al. | Short and efficient synthesis of fluorinated δ-lactams | |
| CN115417802A (en) | Preparation method of sepiatinib and intermediate thereof | |
| CN104837817B (en) | Synthetic route for preparation of 3-amino-piperidine compounds | |
| CN109369678A (en) | A kind of novel synthesis of natural products isomers (-) -6-epi-Porantheridine | |
| CN109134496A (en) | A kind of novel synthesis of natural products (-)-Porantheridine | |
| Oppolzer et al. | Asymmetric synthesis of the spirocyclic core of the cylindricine-type alkaloids | |
| CN110078622A (en) | A kind of synthetic method of 4- ethyoxyl -1,1,2,4,5,6- hexahydro cyclobutane and naphthalene -2- benzoic ether | |
| CN103619847A (en) | Process for the preparation of morphine analogs via metal catalyzed N-demethylation/functionalization and intramolecular group transfer | |
| Wiktelius et al. | Peracid dependent stereoselectivity and functional group contribution to the stereocontrol of epoxidation of (E)-alkene dipeptide isosteres | |
| CN101522679B (en) | Fluorinated catharanthine derivatives, their preparation and their utilisation as vinca dimeric alkaloid precursors | |
| CN106188073B (en) | A kind of ecteinascidin-743 Alkaloid intermediate and its preparation method and application | |
| CN115215814A (en) | Synthetic method of isoxazolidine compounds | |
| Du Ha et al. | Studies of rhodium-catalyzed ring opening of vinyl epoxides | |
| CN111362795B (en) | Preparation method of substituted butyrate derivatives | |
| CN113549051A (en) | Synthesis method of bisamide insecticide | |
| CN109970662B (en) | Method for preparing oxaagoli intermediate | |
| Xiao et al. | Unexpected domino ring closure: highly stereoselective construction of a tetracyclic indole alkaloid ring system | |
| CN110128363B (en) | Cyclosporine derivatives and process for preparing same | |
| CN115477624B (en) | Preparation method of arylamine compound | |
| CN104788370B (en) | A kind of method that configuration controllably synthesizes 2 (4 nitro) bytyry N-oxide compounds |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |