REARRANGEMENT OF 4,5-EPOXY-EUDESMANES WITH BORON TRIFLUORIDE

被引：32

作者：

HIKINO, H

KOHAMA, T

TAKEMOTO, T

机构：

[1] Pharmaceutical Institute, School of Medicine, Tohoku University, Sendai

来源：

TETRAHEDRON | 1969年 / 25卷 / 05期

关键词：

D O I：

10.1016/S0040-4020(01)82676-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Three epoxides (IX, XIX and XX) prepared from the eudesm-4-enes (VIII and XVIII) on treatment with BF3-etherate have been found to undergo skeletal rearrangement resulting in the formation of a number of ketones; i.e. 5-epifaurinan-4-one (X), 1(R)-isopropyl-3-(1′-methyl-5-oxohexylidene)cyclopentane (XI) and 1(S),7(S)-dimethyl-4(R)-isopropyl-bicyclo[5.3.0]decan-6-one (XII) from 4α,5α-epoxy-10-epieudesmane (IX), 1(R),7(S)-dimethyl-4(R)-isopropyl-bicyclo[5.3.0]decan-6-one (XXI) from 4α,5α-epoxy-eudesmane (XIX), and the unsaturated methyl ketone (XI) from 4β,5β-epoxy-eudesmane (XX). © 1969.

引用

页码：1037 / &

共 10 条

[1] REACTIONS OF EPOXIDES .I. REARRANGEMENTS OF SOME 3-SUBSTITUTED 4,5-EPOXY-4-METHYLCHOLESTANES WITH BORON TRIFLUORIDE [J].