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Facile entry to the tetracyclic 5-7-6-3 tigliane ring system
T V Ovaska1, S E Reisman, M A Flynn
1Department of Chemistry, Connecticut College, 270 Mohegan Avenue, New London, Connecticut 06320, USA. tvova@conncoll.edu
Organic Letters
|June 30, 2001
Abstract:
[figure: see text] A tandem anionic 5-exo-dig cyclization/Claisen rearrangement sequence was used to effect a facile, "one-pot" conversion of an appropriately substituted 4-alkyn-1-ol to the tetracyclic carbon core structure of phorbol. The synthesis was conducted using readily available nonracemic starting materials to provide the target structure as a single enantiomer in high chemical yield.