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Asymmetric synthesis of the tricyclic core of NGF-inducing cyathane diterpenes via a transition-metal-catalyzed [5 + 2] cycloaddition.

Authors
  • Wender, P A
  • Bi, F C
  • Brodney, M A
  • Gosselin, F
Type
Published Article
Journal
Organic Letters
Publisher
American Chemical Society
Publication Date
Jun 28, 2001
Volume
3
Issue
13
Pages
2105–2108
Identifiers
PMID: 11418060
Source
Medline
License
Unknown

Abstract

[reaction: see text] A concise asymmetric synthesis of the tricyclic core of cyathane diterpenes is described, based on a novel transition-metal-catalyzed intramolecular [5 + 2] cycloaddition of ynone-vinylcyclopropane 10 (assembled from commercially available (S)-(-)-limonene), which proceeds in 90% yield with >95% selectivity. This strategy provides efficient access (14 steps and 13% overall yield) to potential analogues as well as precursors of nerve growth factor (NGF)-inducing diterpenes.

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