GB966100A - Novel cyclopentanophenanthrene compounds and a process for the production thereof - Google Patents
Novel cyclopentanophenanthrene compounds and a process for the production thereofInfo
- Publication number
- GB966100A GB966100A GB3365860A GB3365860A GB966100A GB 966100 A GB966100 A GB 966100A GB 3365860 A GB3365860 A GB 3365860A GB 3365860 A GB3365860 A GB 3365860A GB 966100 A GB966100 A GB 966100A
- Authority
- GB
- United Kingdom
- Prior art keywords
- keto
- oxido
- androstane
- dione
- group
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 title abstract 3
- 229930194542 Keto Natural products 0.000 abstract 3
- 125000000468 ketone group Chemical group 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- CBMYJHIOYJEBSB-UHFFFAOYSA-N (10S)-3t.17t-Dihydroxy-10r.13c-dimethyl-(5cH.8cH.9tH.14tH)-hexadecahydro-1H-cyclopenta[a]phenanthren Natural products C1C(O)CCC2(C)C3CCC(C)(C(CC4)O)C4C3CCC21 CBMYJHIOYJEBSB-UHFFFAOYSA-N 0.000 abstract 1
- RAJWOBJTTGJROA-UHFFFAOYSA-N (5alpha)-androstane-3,17-dione Natural products C1C(=O)CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CCC21 RAJWOBJTTGJROA-UHFFFAOYSA-N 0.000 abstract 1
- WJIQCDPCDVWDDE-RNQTWYFASA-N (8r,9s,10r,13s,14s)-10,13-dimethyl-5,6,7,8,9,11,12,14,15,16-decahydro-4h-cyclopenta[a]phenanthrene-3,17-dione Chemical compound C1C(=O)C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC21 WJIQCDPCDVWDDE-RNQTWYFASA-N 0.000 abstract 1
- WBEMLZMQSQWKQW-DSORTKNDSA-N [(3S,6R,8R,9S,10R,13S,14S,17S)-17-acetyloxy-6-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate Chemical compound C(C)(=O)O[C@@H]1CC2[C@@H](C[C@H]3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@]2(CC1)C)OC(C)=O)O WBEMLZMQSQWKQW-DSORTKNDSA-N 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000006193 alkinyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000007796 conventional method Methods 0.000 abstract 1
- 125000002993 cycloalkylene group Chemical group 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- OSVMTWJCGUFAOD-KZQROQTASA-N formestane Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1O OSVMTWJCGUFAOD-KZQROQTASA-N 0.000 abstract 1
- 150000004795 grignard reagents Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- JEHCHYAKAXDFKV-UHFFFAOYSA-J lead tetraacetate Chemical compound CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O JEHCHYAKAXDFKV-UHFFFAOYSA-J 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 230000008929 regeneration Effects 0.000 abstract 1
- 238000011069 regeneration method Methods 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 1
- 229920006395 saturated elastomer Chemical group 0.000 abstract 1
- 229910000033 sodium borohydride Inorganic materials 0.000 abstract 1
- 239000012279 sodium borohydride Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Abstract
The invention comprises 6b , 19-oxido androstanes of the general formula: <FORM:0966100/C1/1> in which R represents keto, b -hydroxy or b -acyloxy, R1 represents keto, <FORM:0966100/C1/2> wherein R2 is hydrogen or a saturated or unsaturated aliphatic hydrocarbon group of up to 8 carbon atoms, and when R and R1 are keto, double bonds may be present at C-1,2 or C-1,2 and C-4,5. The compounds may be prepared from 3b , 17b -diacetoxy-androstan-6b -ol by treatment with lead tetra-acetate and saponification of the product to give 6b , 19-oxido-androstane-3b 17b -diol. Oxidation of the latter compound yields the corresponding 3, 17-dione, which may be dehydrogenated to the analogous D 1 and D 1,4-compounds, e.g. via 2, 16-dibromo-6b , 19-oxido androstane-3, 17-dione and 16-bromo-6b , 19-oxido-D 1-androstene-3, 17-dione. The 17-keto group may be protected as a cycloalkylene ketal, the 3-keto group then reduced to 3b -hydroxy with sodium borohydride, and after regeneration of the 17-keto substituent with h-toluenesulphonic acid in acetone, treatment with Grignard reagents yields 6b , 19-oxido androstane-3b , 17b -diols substituted by an alkyl, alkenyl, or alkinyl group in the 17a -position. Esterification by conventional methods gives the corresponding 3-mono- and 3, 17-di-esters. The invention is illustrated by twelve detailed examples.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MX5699860 | 1960-01-06 | ||
| US46076A US3001989A (en) | 1960-01-06 | 1960-07-29 | 6beta,19-oxido androstane derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB966100A true GB966100A (en) | 1964-08-06 |
Family
ID=26640848
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3365860A Expired GB966100A (en) | 1960-01-06 | 1960-09-30 | Novel cyclopentanophenanthrene compounds and a process for the production thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB966100A (en) |
-
1960
- 1960-09-30 GB GB3365860A patent/GB966100A/en not_active Expired
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