On reactions of steroidal 23-oxo and 23,24-epoxysapogenins with Lewis acids.

Abstract:

:The reaction of 23-oxotigogenin acetate with TMSOTf in THF afforded the corresponding bisnorcholanic lactone in 60% yield. The analogous reactions carried out in dichloromethane or benzene gave the rearranged products--the isomeric spirostanic ketone (10-15%) and bisfuran (40-42%). Similar products were also obtained upon treatment of 23,24-epoxysapogenins with BF(3). The epoxides treated with TiCl(4) afforded mostly chlorohydrins and no rearranged products were detected.

journal_name

Steroids

journal_title

Steroids

authors

Jastrzebska I,Siergiejczyk L,Tomkiel AM,Urbańczyk-Lipkowska Z,Wójcik D,Morzycki JW

doi

10.1016/j.steroids.2009.02.010

subject

Has Abstract

pub_date

2009-08-01 00:00:00

pages

675-83

issue

8

eissn

0039-128X

issn

1878-5867

pii

S0039-128X(09)00060-9

journal_volume

74

pub_type

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