STRUCTURE AND FUNCTION OF ESTROGENS .1. SYNTHESIS OF 4B-METHYL-TRANS-4B,5,6,10B,11,12-HEXAHYDROCHRYSENE-2,8-DIOL

被引：13

作者：

COLLINS, DJ

MATTHEWS, WA

机构：

[1] Department of Chemistry, Monash University, Clayton, VIC

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 1979年 / 32卷 / 05期

关键词：

D O I：

10.1071/CH9791093

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Oxidation of 2, 8-dimethoxy-5, 6, ll, 12-tetrahydrochrysene (17) with m-chloroperbenzoic acid gave 2, 8-dimethoxy-4b, 5, 6, 10b, ll, 12-hexahydro-4b, 10b-epoxychrysene (20). Treatment of this with methylmagnesium bromide afforded an inseparable mixture of 2, 8-dimethoxy-4b-methyl-4b, 5, 6, 12- tetrahydrochrysene (28) and 2, 8-dimethoxy-5, 6-dihydrochrysene (18) in the ratio 7:3. Hydrogenation of this mixture over 10% palladium-charcoal gave 2, 8-dimethoxy-4b-methyl-trans-4b, 5, 6, 10b, ll, 12- hexahydrochrysene (30) which was readily separable from (18). Demethylation of compound (30) yielded 4b-methyl-trans-4b, 5, 6, 10b, ll, 12-hexahydrochrysene-2, 8-dioI (11a), which was required for assay as an oestrogen. © 1979 ASEG.

引用

页码：1093 / 1106

页数：14

共 20 条

[1] SIMPLE PROCEDURE FOR EPOXIDATION OF ACID-SENSITIVE OLEFINIC COMPOUNDS WITH META-CHLOROPERBENZOIC ACID IN AN ALKALINE BIPHASIC SOLVENT SYSTEM [J].