Enantiospecific Synthesis of a Chiral Intermediate in Steroid Synthesis

J. Andrew Clase; Thomas Money

doi:10.1055/s-1989-27434

Synthesis 1989; 1989(12): 934-936
DOI: 10.1055/s-1989-27434

communication

© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Enantiospecific Synthesis of a Chiral Intermediate in Steroid Synthesis

J. Andrew Clase^* , Thomas Money

^*Chemistry Department, University of British Columbia, 2036 Main Mall, Vancouver, British Columbia, V6T 1Y6, Canada

Abstract

PDF Download All articles of this category

An enantiospecific route to a potentially useful intermediate 13 in the intramolecular Diels-Alder route to steroids is described. The key step involves efficient ring cleavage of 9,10-dibromocamphor (7) to provide a monocyclic bromoester 8 of defined chirality. This is readily transformed to 13.

PDF (227 kb)