TOTAL SYNTHESIS OF 14-ALPHA-HYDROXYESTRONE 3-METHYL ETHER

被引：20

作者：

KAMETANI, T

NEMOTO, H

TSUBUKI, M

PURVANECKAS, GE

AIZAWA, M

NISHIUCHI, M

机构：

[1] Pharmaceutical Institute, Tohoku University, Aobayama

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1979年 / 11期

关键词：

D O I：

10.1039/p19790002830

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Total synthesis of 14α-hydroxyestrone 3-methyl ether (5) was achieved by the thermolysis of 2-[2-(1,2-dihydro-4-methoxybenzocyclobuten-1-yl)ethyl]-3- hydroxy-2-methyl-3-vinylcyclopentan-1-one (27), obtained by Grignard reaction of 2-[2-(1,2-dihydro-4-methoxybenzocyclobuten-1-yl)ethyl]-2-methylcyclopentane-1, 3-dione (26) with vinylmagnesium bromide. An alternative synthesis of (5) started from authentic 14-dehydroestradiol bis-(t-butyldimethylsilyl) ether (28) and proceeded through estradiol-14α,15α-epoxide 3-methyl 17β-t-butyldimethylsilyl bisether (31).

引用

页码：2830 / 2835

页数：6

共 23 条

[1] TOTAL SYNTHESIS OF STEROIDS .6. SYNTHESIS OF 14BETA-HYDROXY-3-METHOXYESTRA-1,3,5(10)-TRIENE-11,17-DIONE AND RELATED COMPOUNDS [J].