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Dienyne ring-closing metathesis approach for the construction of taxosteroids.

Authors
  • Aldegunde, María J
  • García-Fandiño, Rebeca
  • Castedo, Luis
  • Granja, Juan R
Type
Published Article
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
Publication Date
Jan 01, 2007
Volume
13
Issue
18
Pages
5135–5150
Identifiers
PMID: 17385199
Source
Medline
License
Unknown

Abstract

A cascade dienyne ring-closing metathesis approach has been applied to the synthesis of the tetracyclic carbon framework of a new class of hybrid compounds-the taxosteroids-possessing carbon frameworks incorporating moieties characteristic of both taxanes (such as AB rings) and steroids (i.e., CD system and side chain). This tandem cyclization is highly stereoselective, allowing the one-step formation of the bicyclo[5.3.1]undecene system characteristic of taxol. In this work we describe the scope and limitations of such cyclizations.

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