DE3240054A1 - Verfahren zur herstellung von 8.12-epoxy-13.14.15.16-tetranorlabdan - Google Patents
Verfahren zur herstellung von 8.12-epoxy-13.14.15.16-tetranorlabdanInfo
- Publication number
- DE3240054A1 DE3240054A1 DE19823240054 DE3240054A DE3240054A1 DE 3240054 A1 DE3240054 A1 DE 3240054A1 DE 19823240054 DE19823240054 DE 19823240054 DE 3240054 A DE3240054 A DE 3240054A DE 3240054 A1 DE3240054 A1 DE 3240054A1
- Authority
- DE
- Germany
- Prior art keywords
- epoxy
- norambreinolide
- tetranorlabdane
- acid
- tetranorlabdan
- 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.)
- Withdrawn
Links
- 238000004519 manufacturing process Methods 0.000 title description 6
- 239000002253 acid Substances 0.000 claims description 20
- IMKJGXCIJJXALX-SHUKQUCYSA-N Norambreinolide Chemical compound CC([C@@H]1CC2)(C)CCC[C@]1(C)[C@@H]1[C@]2(C)OC(=O)C1 IMKJGXCIJJXALX-SHUKQUCYSA-N 0.000 claims description 18
- IMKJGXCIJJXALX-UHFFFAOYSA-N ent-Norambreinolide Natural products C1CC2C(C)(C)CCCC2(C)C2C1(C)OC(=O)C2 IMKJGXCIJJXALX-UHFFFAOYSA-N 0.000 claims description 18
- 238000007363 ring formation reaction Methods 0.000 claims description 12
- 150000002009 diols Chemical class 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 3
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 235000005505 Ziziphus oenoplia Nutrition 0.000 claims 1
- 244000104547 Ziziphus oenoplia Species 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 10
- -1 lithium aluminum hydride Chemical compound 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- FOFMBFMTJFSEEY-YFVJMOTDSA-N (2e,6e)-1-bromo-3,7,11-trimethyldodeca-2,6,10-triene Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CBr FOFMBFMTJFSEEY-YFVJMOTDSA-N 0.000 description 5
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000012280 lithium aluminium hydride Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- FQTLCLSUCSAZDY-UHFFFAOYSA-N (+) E(S) nerolidol Natural products CC(C)=CCCC(C)=CCCC(C)(O)C=C FQTLCLSUCSAZDY-UHFFFAOYSA-N 0.000 description 3
- CRDAMVZIKSXKFV-FBXUGWQNSA-N (2-cis,6-cis)-farnesol Chemical compound CC(C)=CCC\C(C)=C/CC\C(C)=C/CO CRDAMVZIKSXKFV-FBXUGWQNSA-N 0.000 description 3
- 239000000260 (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol Substances 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- FQTLCLSUCSAZDY-ATGUSINASA-N Nerolidol Chemical compound CC(C)=CCC\C(C)=C\CC[C@](C)(O)C=C FQTLCLSUCSAZDY-ATGUSINASA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229930002886 farnesol Natural products 0.000 description 3
- 229940043259 farnesol Drugs 0.000 description 3
- WASNIKZYIWZQIP-AWEZNQCLSA-N nerolidol Natural products CC(=CCCC(=CCC[C@@H](O)C=C)C)C WASNIKZYIWZQIP-AWEZNQCLSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 3
- CXMUQCRSSKJBHD-NCZFFCEISA-N (3e,7e)-4,8,12-trimethyltrideca-3,7,11-trienenitrile Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CC#N CXMUQCRSSKJBHD-NCZFFCEISA-N 0.000 description 2
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
- 150000003606 tin compounds Chemical class 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- LFJNYXULIVRJPP-UHFFFAOYSA-N C(C(Cl)(Cl)Cl)O[SnH3] Chemical compound C(C(Cl)(Cl)Cl)O[SnH3] LFJNYXULIVRJPP-UHFFFAOYSA-N 0.000 description 1
- HREYUWIJMNUMON-UHFFFAOYSA-N C(CC(Cl)(Cl)Cl)CO[SnH3] Chemical compound C(CC(Cl)(Cl)Cl)CO[SnH3] HREYUWIJMNUMON-UHFFFAOYSA-N 0.000 description 1
- LWANBDBGRZMLSW-UHFFFAOYSA-N CC(=CCC#N)CCC=C(CCC=C(C)C)C.[C-]#N Chemical compound CC(=CCC#N)CCC=C(CCC=C(C)C)C.[C-]#N LWANBDBGRZMLSW-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 229910021623 Tin(IV) bromide Inorganic materials 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- MBZDUPZMDJXUNK-UHFFFAOYSA-L dimethoxytin(2+);dichloride Chemical compound CO[Sn](Cl)(Cl)OC MBZDUPZMDJXUNK-UHFFFAOYSA-L 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- IGWPDTLXMSRIJG-UHFFFAOYSA-J phenoxytin(3+);trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Sn+3]OC1=CC=CC=C1 IGWPDTLXMSRIJG-UHFFFAOYSA-J 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- LTSUHJWLSNQKIP-UHFFFAOYSA-J tin(iv) bromide Chemical compound Br[Sn](Br)(Br)Br LTSUHJWLSNQKIP-UHFFFAOYSA-J 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
- WWMIMCSJXFHRJW-UHFFFAOYSA-N trichloromethoxystannane Chemical compound ClC(Cl)(Cl)O[SnH3] WWMIMCSJXFHRJW-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/92—Naphthofurans; Hydrogenated naphthofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/10—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
- Furan Compounds (AREA)
- Pyrane Compounds (AREA)
- Fats And Perfumes (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823240054 DE3240054A1 (de) | 1982-10-28 | 1982-10-28 | Verfahren zur herstellung von 8.12-epoxy-13.14.15.16-tetranorlabdan |
| JP58128083A JPS5982381A (ja) | 1982-10-28 | 1983-07-15 | ８，１２−エポキシ−１３，１４，１５，１６−テトラノルラブダンの製法 |
| US06/517,980 US4503240A (en) | 1982-10-28 | 1983-07-28 | Process for preparing 8,12-epoxy-13,14,15,16-tetranorlabdane |
| DE8383110737T DE3368627D1 (en) | 1982-10-28 | 1983-10-27 | Process for the preparation of 8,12-epoxy-13,14,15,16-tetranor labdane |
| EP83110737A EP0107857B1 (de) | 1982-10-28 | 1983-10-27 | Verfahren zur Herstellung von 8.12-Epoxy-13.14.15.16-tetranorlabdan |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823240054 DE3240054A1 (de) | 1982-10-28 | 1982-10-28 | Verfahren zur herstellung von 8.12-epoxy-13.14.15.16-tetranorlabdan |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3240054A1 true DE3240054A1 (de) | 1984-05-03 |
Family
ID=6176882
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19823240054 Withdrawn DE3240054A1 (de) | 1982-10-28 | 1982-10-28 | Verfahren zur herstellung von 8.12-epoxy-13.14.15.16-tetranorlabdan |
| DE8383110737T Expired DE3368627D1 (en) | 1982-10-28 | 1983-10-27 | Process for the preparation of 8,12-epoxy-13,14,15,16-tetranor labdane |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8383110737T Expired DE3368627D1 (en) | 1982-10-28 | 1983-10-27 | Process for the preparation of 8,12-epoxy-13,14,15,16-tetranor labdane |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4503240A (enExample) |
| EP (1) | EP0107857B1 (enExample) |
| JP (1) | JPS5982381A (enExample) |
| DE (2) | DE3240054A1 (enExample) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4918205A (en) * | 1987-09-30 | 1990-04-17 | Basf Aktiengesellschaft | Preparation of alkylated dodechydronaphto[2,1-b]furans |
| DE4123767A1 (de) * | 1991-07-18 | 1993-01-21 | Henkel Kgaa | Verfahren zur herstellung von 8,12-oxido-13,14,15,16-tetranorlabdan |
| US5292902A (en) * | 1991-08-02 | 1994-03-08 | Givaudan-Roure Corporation | Process for the manufacture of odorants and intermediates used therein |
| DE4301555C1 (de) * | 1993-01-21 | 1994-07-07 | Henkel Kgaa | Verfahren zur Herstellung von Norambreinolid |
| US5329053A (en) * | 1992-09-03 | 1994-07-12 | Givaudan-Roure Corporation | Process for the manufacture of known odorants |
| US5616737A (en) * | 1995-07-06 | 1997-04-01 | Basf Aktiengesellschaft | Stereoselective preparation of (-) 3a,6,6,9a-tetramethyl-perhydronaphtho[2,1-b]furan |
| WO2008015977A1 (fr) | 2006-07-31 | 2008-02-07 | Kao Corporation | PROCÉDÉ POUR LA PRODUCTION DE (±)-3a,6,6,9a-TÉTRAMÉTHYLDÉCAHYDRONAPHTO[2,1-b]FURAN-2(1H)-ONE |
| WO2012085056A1 (en) | 2010-12-21 | 2012-06-28 | Givaudan Sa | 2-(alkoxy or aryloxy carbonyl)-4-methyl-6-(2,6,6-trimethylcyclohex-1-enyl)hex-2-enoic acid compounds, its preparation and use |
| WO2022136227A1 (en) | 2020-12-22 | 2022-06-30 | Givaudan Sa | Process of making organic compounds |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60239481A (ja) * | 1984-05-14 | 1985-11-28 | T Hasegawa Co Ltd | （±）−アンブロツクスの製法及びその利用 |
| JPH03502456A (ja) * | 1988-11-30 | 1991-06-06 | タシケントスキ ゴスダルストベンニ ウニベルシテト イメニ ベー．イー．レニナ | ３，１８‐ジヒドロキシ‐９，１３‐エポキシラブダン誘導体，それらの調製方法およびそれらに基づく止血医薬製剤 |
| ES2098232T3 (es) * | 1989-06-19 | 1997-05-01 | Firmenich & Cie | Carbinoles cicloalifaticos y su utilizacion a titulo de productos de partida para la preparacion de derivados furanicos. |
| US5326888A (en) * | 1990-10-09 | 1994-07-05 | Henkel Research Corporation | Carbonylation of allylic alcohols and synthesis of an ambergris fragance compound |
| WO1993021174A1 (de) * | 1992-04-16 | 1993-10-28 | Henkel Kommanditgesellschaft Auf Aktien | Verfahren zur herstellung von sclareolid |
| ES2238003B2 (es) * | 2004-01-22 | 2006-04-01 | Universidad De Jaen | Procedimientos de obtencion de norambreinolida enantiomericamente pura y racemica. |
| US9376365B2 (en) | 2012-11-23 | 2016-06-28 | Firmenich Sa | Hydrocarbonylation or methoxycarbonylation of 1,3-diene derivatives with palladium complex |
| MX361536B (es) * | 2015-10-23 | 2018-12-10 | Univ Michoacana De San Nicolas De Hidalgo | Proceso de sintesis de ambrox a partir de ageratina jocotepecana. |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3029255A (en) * | 1950-10-24 | 1962-04-10 | Firmenick & Co | Compounds having an ambergris scent and their preparation process |
-
1982
- 1982-10-28 DE DE19823240054 patent/DE3240054A1/de not_active Withdrawn
-
1983
- 1983-07-15 JP JP58128083A patent/JPS5982381A/ja active Granted
- 1983-07-28 US US06/517,980 patent/US4503240A/en not_active Expired - Fee Related
- 1983-10-27 EP EP83110737A patent/EP0107857B1/de not_active Expired
- 1983-10-27 DE DE8383110737T patent/DE3368627D1/de not_active Expired
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4918205A (en) * | 1987-09-30 | 1990-04-17 | Basf Aktiengesellschaft | Preparation of alkylated dodechydronaphto[2,1-b]furans |
| DE4123767A1 (de) * | 1991-07-18 | 1993-01-21 | Henkel Kgaa | Verfahren zur herstellung von 8,12-oxido-13,14,15,16-tetranorlabdan |
| US5470989A (en) * | 1991-07-18 | 1995-11-28 | Henkel Kommanditgesellschaft Auf Aktien | Process for the production of mixtures of stereoisomers of 8,12-oxido-13,14,15,16-tetranorlabdane |
| US5292902A (en) * | 1991-08-02 | 1994-03-08 | Givaudan-Roure Corporation | Process for the manufacture of odorants and intermediates used therein |
| US5329053A (en) * | 1992-09-03 | 1994-07-12 | Givaudan-Roure Corporation | Process for the manufacture of known odorants |
| DE4301555C1 (de) * | 1993-01-21 | 1994-07-07 | Henkel Kgaa | Verfahren zur Herstellung von Norambreinolid |
| US5616737A (en) * | 1995-07-06 | 1997-04-01 | Basf Aktiengesellschaft | Stereoselective preparation of (-) 3a,6,6,9a-tetramethyl-perhydronaphtho[2,1-b]furan |
| WO2008015977A1 (fr) | 2006-07-31 | 2008-02-07 | Kao Corporation | PROCÉDÉ POUR LA PRODUCTION DE (±)-3a,6,6,9a-TÉTRAMÉTHYLDÉCAHYDRONAPHTO[2,1-b]FURAN-2(1H)-ONE |
| WO2012085056A1 (en) | 2010-12-21 | 2012-06-28 | Givaudan Sa | 2-(alkoxy or aryloxy carbonyl)-4-methyl-6-(2,6,6-trimethylcyclohex-1-enyl)hex-2-enoic acid compounds, its preparation and use |
| US8933253B2 (en) | 2010-12-21 | 2015-01-13 | Givaudan S.A. | 2-(Alkoxy or aryloxy carbonyl)-4-methyl-6-(2,6,6-trimethylcyclohex-1-enyl)hex-2-enoic acid compunds, its preparation and use |
| US9163000B2 (en) | 2010-12-21 | 2015-10-20 | Givaudan S.A. | 2-(alkoxy or aryloxy carbonyl)-4-methyl-6-(2,6.6-trimethylcyclohex-1- enyl)hex-2-enoic acid compounds, its preparation and use |
| US9732056B2 (en) | 2010-12-21 | 2017-08-15 | Givaudan, S.A. | 2-(alkoxy or aryloxy carbonyl)-4-methyl-6-(2,6,6-trimethylcyclohex-1-enyl)hex-2-enoic acid compounds, its preparation and use |
| US10081613B2 (en) | 2010-12-21 | 2018-09-25 | Givaudan, S.A. | 2-(alkoxy or aryloxy carbonyl)-4-methyl-6-(2,6,6-trimethylcyclohex-1-enyl)hex-2-enoic acid compounds, its preparation and use |
| WO2022136227A1 (en) | 2020-12-22 | 2022-06-30 | Givaudan Sa | Process of making organic compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0107857A1 (de) | 1984-05-09 |
| DE3368627D1 (en) | 1987-02-05 |
| JPS5982381A (ja) | 1984-05-12 |
| EP0107857B1 (de) | 1986-12-30 |
| US4503240A (en) | 1985-03-05 |
| JPS611432B2 (enExample) | 1986-01-17 |
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