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Synthesis of Novel 5α,9α‐Bridged Steroids by a Boron Trifluoride−Diethyl Ether Induced Rearrangement
Author(s) -
Bondarenko Lidija,
Lorenc Ljubinka,
Bläser Dieter,
Boese Roland
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400117
Subject(s) - chemistry , boron trifluoride , diethyl ether , ether , stereoselectivity , boron , steroid , medicinal chemistry , organic chemistry , stereochemistry , catalysis , biochemistry , hormone
A stereoselective and synthetically useful rearrangement reaction of 5α,8α‐bridged 9,11α‐epoxy steroids induced by boron trifluoride−diethyl ether is presented, in the preparation of a new class of 5α,9α‐bridged 11α‐hydroxy steroid derivatives in high yields. Lactones were prepared from several of the rearranged 11α‐hydroxy compounds. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)