PL210282B1 - New (4aR,7R)-(-)-4,4a,5,6,7,8-hexahydro-7ß-hydroxyl-4a-methyl-2-(3H)-naphtalenone and method for its manufacture - Google Patents
New (4aR,7R)-(-)-4,4a,5,6,7,8-hexahydro-7ß-hydroxyl-4a-methyl-2-(3H)-naphtalenone and method for its manufactureInfo
- Publication number
- PL210282B1 PL210282B1 PL378554A PL37855405A PL210282B1 PL 210282 B1 PL210282 B1 PL 210282B1 PL 378554 A PL378554 A PL 378554A PL 37855405 A PL37855405 A PL 37855405A PL 210282 B1 PL210282 B1 PL 210282B1
- Authority
- PL
- Poland
- Prior art keywords
- hexahydro
- methyl
- naphthalenone
- new
- hydroxy
- Prior art date
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Description
Przedmiotem wynalazku jest nowy (4aR,7R)-(-)-4,4a,5,6,7,8-heksahydro-7e-hydroksy-4a-metylo-2-(3H)-naftalenon, o wzorze 2 przedstawionym na rysunku, i sposób jego wytwarzania.The subject of the invention is a new (4aR, 7R) - (-) - 4,4a, 5,6,7,8-hexahydro-7e-hydroxy-4a-methyl-2- (3H) -naphthalenone, with the formula 2 shown in the figure and the method of its production.
Związek ten może znaleźć zastosowanie, jako chiralny substrat w totalnej syntezie związków o wysokiej aktywności biologicznej, np. terpenoidów oraz steroidów.This compound may find use as a chiral substrate in the total synthesis of compounds with high biological activity, e.g. terpenoids and steroids.
W dostępnej literaturze nie znaleziono doniesień o otrzymaniu (4aR,7R)-(-)-4,4a,5,6,7,8-heksahydro-7e-hydroksy-4a-metylo-2(3H)-naftalenonu.There are no reports of obtaining (4aR, 7R) - (-) - 4,4a, 5,6,7,8-hexahydro-7e-hydroxy-4a-methyl-2 (3H) -naphthalenone in the available literature.
Istotą wynalazku jest nowy (4aR,7R)-(-)-4,4a,5,6,7,8-heksahydro-7e-hydroksy-4a-metylo-2(3H)-naftalenon, o wzorze 2 przedstawionym na rysunku.The essence of the invention is a new (4aR, 7R) - (-) - 4,4a, 5,6,7,8-hexahydro-7e-hydroxy-4a-methyl-2 (3H) -naphthalenone, represented by the formula 2 shown in the drawing.
Istotą wynalazku jest też sposób wytwarzania nowego (4aR,7R)-(-)-4,4a,5,6,7,8-heksahydro-7e-hydroksy-4a-metylo-2-(3H)-naftalenonu. Sposób, według wynalazku, polega na tym, że regioselektywną hydroksylację (R)-(-)-4,4a,5,6,7,8-heksahydro-4a-metylo-2-(3H)-naftalenonu prowadzi się za pomocą kultury szczepu Chaetomium sp. 1.The essence of the invention is also the method of producing new (4aR, 7R) - (-) - 4,4a, 5,6,7,8-hexahydro-7e-hydroxy-4a-methyl-2- (3H) -naphthalenone. The method according to the invention consists in that the regioselective hydroxylation of (R) - (-) - 4,4a, 5,6,7,8-hexahydro-4a-methyl-2- (3H) -naphthalenone is carried out with a culture Chaetomium sp. 1 strain.
Korzystne jest, gdy hydroksylację prowadzi się wodną kulturą szczepu, przy ciągłym mieszaniu reagentów, w temperaturze 288 - 308 K.It is preferable that the hydroxylation is carried out with the aqueous strain, under constant stirring of the reactants, at a temperature of 288-308 K.
Postępując zgodnie z wynalazkiem, w wyniku działania układu enzymatycznego zawartego w komórkach grzyba Chaetomium sp. 1, następuje regioselektywna hydroksylacja substratu w pozycji 7β. Uzyskany w ten sposób produkt wydziela się z wodnej kultury mikroorganizmu znanym sposobem przez ekstrakcję chloroformem.Proceeding according to the invention, as a result of the action of the enzyme system contained in the Chaetomium sp. 1 fungal cells, regioselective hydroxylation of the substrate in the 7β position takes place. The product obtained in this way is separated from the aqueous culture of the microorganism by a known method by extraction with chloroform.
Będący przedmiotem wynalazku (4aR,7R)-(-)-4,4a,5,6,7,8-heksahydro-7e-hydroksy-4a-metylo-2-(3H)-naftalenon może znaleźć zastosowanie np. jako chiralny substrat w totalnej syntezie bardziej skomplikowanej związków o wysokiej aktywności biologicznej z grupy: steroidów, alkaloidów oraz terpenoidów (M. Pufa, G. Revial, A. Gumgant, J. d'Angelo; J. Am. Chem. Soc, 1986, vol. 107).The (4aR, 7R) - (-) - 4,4a, 5,6,7,8-hexahydro-7e-hydroxy-4a-methyl-2- (3H) -naphthalenone being the subject of the invention can be used e.g. as a chiral substrate in the total synthesis of more complex compounds with high biological activity from the group of: steroids, alkaloids and terpenoids (M. Pufa, G. Revial, A. Gumgant, J. d'Angelo; J. Am. Chem. Soc, 1986, vol. 107 ).
Zasadniczą zaletą wynalazku jest otrzymanie (4aR,7R)-(-)-4,4a,5,6,7,8-heksahydro-7e-hydroksy-4a-metylo-2-(3H)-naftalenonu jako głównego produktu reakcji, z wydajnością 50%, w temperaturze pokojowej i pH bliskim obojętnemu.The main advantage of the invention is the preparation of (4aR, 7R) - (-) - 4,4a, 5,6,7,8-hexahydro-7e-hydroxy-4a-methyl-2- (3H) -naphthalenone as the main reaction product, 50% yield, at room temperature and near neutral pH.
Wynalazek jest bliżej objaśniony na przykładzie wykonania.The invention is explained in more detail using an exemplary embodiment.
P r z y k ł a d. Do kolby Erlenmajera o pojemności 250 cm3, w której znajduje się 100 cm3 sterylnej pożywki zawierającej 3 g glukozy i 1 g aminobaku, wprowadza się szczep Chaetomium sp. 1. Po trzech dniach wzrostu dodaje się 50 mg (R)-(-)-4,4a,5,6,7,8-heksahydro-4a-metylo-2(3H)-naftalenonu, o wzorze 1, rozpuszczonego w 1 cm3 acetonu. Transformację prowadzi się przy ciągłym wstrząsaniu przez 6 dni. Następnie uzyskany roztwór transformacyjny ekstrahuje się trzykrotnie chloroformem, osusza bezwodnym siarczanem magnezu i odparowuje rozpuszczalnik. Otrzymuje się 61 mg surowego produktu, który oczyszcza się chromatograficznie, jako eluentu używa się mieszaniny heksan-aceton, w stosunku 2:1. Na tej drodze otrzymuje się 25,2 mg (4aR,7R)-(-)-4,4a,5,6,7,8-heksahydro-7e-hydroksy-4a-metylo-2-(3H)-naftalenonu (wydajność przekracza 50%).Example d. To the Erlenmeyer flask with a capacity of 250 cm 3, which is 100 cm 3 of sterile medium containing 3 g of glucose and 1 g aminobaku introduced into a strain of Chaetomium sp. 1. After three days of growth is added 50 mg of ( R) - (-) - 4,4a, 5,6,7,8-hexahydro-4a-methyl-2 (3H) -naphthalenone of formula 1, dissolved in 1 cm 3 of acetone. The transformation is carried out under continuous shaking for 6 days. The resulting transformation solution was then extracted three times with chloroform, dried with anhydrous magnesium sulfate, and the solvent was evaporated. 61 mg of crude product are obtained, which product is purified by chromatography using a 2: 1 hexane-acetone mixture as eluent. In this way, 25.2 mg of (4aR, 7R) - (-) - 4.4a, 5,6,7,8-hexahydro-7e-hydroxy-4a-methyl-2- (3H) -naphthalenone are obtained (yield exceeds 50%).
Uzyskany produkt charakteryzuje się następującymi danymi spektralnymi:The obtained product is characterized by the following spectral data:
1H NMR (500 MHz, CDCI3) δ (ppm); 1,21 (s, 3H); 1,34 (td, 1H, J = 14,4 Hz, J = 3,6Hz); 1,62-1,81 (m, 4H); 1,87-1,92 (m, 1H); 2,38-2,36 (m, 3H); 2,46 (ddd, 1H, J = 17,1 Hz, J = 14,0 Hz, J = 5,6 Hz); 2,51 (ddd, 1H, J = 14,0 Hz, J = 4,6 Hz, J = 2,5 Hz); 3,57 (tt, 1H, J = 11,1 Hz, J = 4,8 Hz); 5,72 (s, 1H). 1 H NMR (500 MHz, CDCl 3) δ (ppm); 1.21 (s. 3H); 1.34 (td, 1H, J = 14.4Hz, J = 3.6Hz); 1.62-1.81 (m, 4H); 1.87-1.92 (m, 1H); 2.38-2.36 (m, 3H); 2.46 (ddd, 1H, J = 17.1 Hz, J = 14.0 Hz, J = 5.6 Hz); 2.51 (ddd, 1H, J = 14.0 Hz, J = 4.6 Hz, J = 2.5 Hz); 3.57 (mp, 1H, J = 11.1Hz, J = 4.8Hz); 5.72 (s, 1H).
Claims (4)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL378554A PL210282B1 (en) | 2005-12-28 | 2005-12-28 | New (4aR,7R)-(-)-4,4a,5,6,7,8-hexahydro-7ß-hydroxyl-4a-methyl-2-(3H)-naphtalenone and method for its manufacture |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL378554A PL210282B1 (en) | 2005-12-28 | 2005-12-28 | New (4aR,7R)-(-)-4,4a,5,6,7,8-hexahydro-7ß-hydroxyl-4a-methyl-2-(3H)-naphtalenone and method for its manufacture |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL378554A1 PL378554A1 (en) | 2006-06-26 |
| PL210282B1 true PL210282B1 (en) | 2011-12-30 |
Family
ID=38739820
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL378554A PL210282B1 (en) | 2005-12-28 | 2005-12-28 | New (4aR,7R)-(-)-4,4a,5,6,7,8-hexahydro-7ß-hydroxyl-4a-methyl-2-(3H)-naphtalenone and method for its manufacture |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL210282B1 (en) |
-
2005
- 2005-12-28 PL PL378554A patent/PL210282B1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| PL378554A1 (en) | 2006-06-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN106188078A (en) | A kind of chiral spiro hydroxyindole benzopyrone the synthetic method of 3,4 dihydropyrane compounds | |
| PL210282B1 (en) | New (4aR,7R)-(-)-4,4a,5,6,7,8-hexahydro-7ß-hydroxyl-4a-methyl-2-(3H)-naphtalenone and method for its manufacture | |
| PL213614B1 (en) | new 7-0-n-D-4 methoxyglucopiranozide 8- prenylonaringenines and the manner of their manfacturing | |
| Wang et al. | Synthesis of trifluoromethylated analogues of β-l-fucofuranose and β-l-4, 6-dideoxyxylohexopyranose | |
| PL195347B1 (en) | Method of manufacturing s(s+)-1,2,3,4-tetrahydro-1-naphtol | |
| PL207190B1 (en) | Method for manufacturing naphtalenone (4aS, 6S)-4,4a, 5,6,7,8-hexahydro-6-hydroxyl-4a-methyl-2 (3H) | |
| PL223446B1 (en) | 4'-O-β-D-glucopyranosylxanthohumol C and a method for its manufacturing | |
| PL207193B1 (en) | Method for the manufacture of (4aR,6R)-(-)-4,4a,5,6,7,8-hexahydro-6ß-hydroxyl-4a-methyl-2-(3H)-naphtalenone | |
| PL207817B1 (en) | Method for the manufacture of S-(-)-6-chloro-1, 2, 3, 4-tetrahydro-2-naphtol | |
| PL223444B1 (en) | Method for preparing 1",2",α,β-tetrahydroxanthohumol C | |
| PL223441B1 (en) | 4'-O-β-D-glucopyranosyl-4, 2'-dihydroxy-6'-methoxy-3'-prenyl-α, β-dihydrochalcone and a process for its preparation | |
| PL207816B1 (en) | Method for the manufacture of S-(-)-7-methoxy-1, 2, 3, 4-tetrahydro-2-naphtol | |
| PL207814B1 (en) | Production method of S-(-)-8-metoxy-2tetralol | |
| PL207815B1 (en) | Method for the manufacture of S-(-)-6-methoxy-1, 2, 3, 4-tetrahydro-2-naphtol | |
| PL222788B1 (en) | 4'-0-β-D-4'' '-methoxy-glucopyranosyl-4, 2'-dihydroxy-6'-methoxy-3'-prenyl-α, β-dihydrochalcone and a process for its preparation | |
| PL197575B1 (en) | Method for manufacture of s-(-)-1-(2-naphtyl)ethanol | |
| PL192228B1 (en) | Novel 8ß-hydroxy-1-dehydroandrostendione and method of obtaining same | |
| PL207820B1 (en) | Method for the obtainment of S-(+)-5-metoxy-1-tetralole | |
| PL237132B1 (en) | 7-O-β-D-4''-O-methyl-glucopyranosyl-3',4',5-trihydroxyflavanone and method for obtaining 7-O-β-D-4''-O-methyl-glucopyranosyl-3',4',5-trihydroxyflavanone | |
| PL237131B1 (en) | Method for obtaining 3'-O-β-D-glucopyranosyl-4',5.7-trihydroxyflavanone | |
| PL215792B1 (en) | (Z)-6-sulfate-6,4'-dihydroxy-7-prenyl-4-metoksyaurone and process for the preparation thereof | |
| PL218593B1 (en) | Process for obtaining of 4'-hydroxy-7,8-benzoflavone | |
| PL207821B1 (en) | Method for the manufacture of S-(-)-8-methoxy-1, 2, 3, 4-tetrahydro-2-naphtol | |
| PL223442B1 (en) | 4'-O-β-D-glucopyranosyl-1",2"-dihydroxanthohumol K and its manufacturing process | |
| PL210638B1 (en) | New 7-O- -D-4-isoxantohumol methoxyglucopyranozid and its production method |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LICE | Declarations of willingness to grant licence |
Effective date: 20110811 |
|
| LAPS | Decisions on the lapse of the protection rights |
Effective date: 20081228 |