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Synthetic studies on the ingenane diterpenes. An improved entry into a trans-intrabridgehead system
James H Rigby1, Bérangère Bazin, J Hoyt Meyer
1Department of Chemistry, Wayne State University, Detroit, Michigan 48202-3489, USA. jhr@chem.wayne.edu
Organic Letters
|March 1, 2002
Abstract:
[reaction: see text] The efficient construction of an ingenol intermediate exhibiting "insideminus signoutside" intrabridgehead stereochemistry is reported. The sequence features the net conversion of a cis-intrabridgehead compound into a highly strained trans-species via palladium-mediated isomerization of an allylic epoxide followed by a low-temperature alkoxide-accelerated 1,5-hydrogen migration.