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