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Synthesis of bicyclic gamma-ylidenetetronates
Francisco Velázquez1, Horacio F Olivo
1Division of Medicinal and Natural Products Chemistry, College of Pharmacy, The University of Iowa, Iowa City 52242, USA.
Organic Letters
|September 14, 2002
Abstract:
The bicyclic gamma-ylidenetetronate motif found in several Stemona alkaloids was prepared in a stereoselective manner by addition of lithium methyl tetronate to an alkoxy oxonium ion formed from a lactone. The corresponding mixed alkyl ketal obtained was subjected to a Lewis acid-base-promoted dealkoxylation reaction to deliver the desired products.