Application of the Rh(ll)-Cyclization/Cycloaddition Cascade for the Total Synthesis of (±)-Aspidophytine

• Authors: Jose M. Mejia-Oneto, Emory University; Albert Padwa, Emory University
• Journal Title: Organic Letters
• Volume: Volume 8, Number 15
• Publisher: American Chemical Society | 2006-07-20, Pages 3275-3278
• Type of Work: Article | Post-print: After Peer Review
• Publisher DOI: http://doi.org/10.1021/ol061137i
• Subjects: Chemistry, General

Abstract

A new strategy for the synthesis of (±)-aspidophytine has been developed and is based on a Rh(ll)-catalyzed cyclization/dipolar-cycloaddition sequence. The resulting [3+2]-cycloadduct undergoes an efficient Lewis acid mediated cascade that rapidly provides the complete skeleton of aspidophytine. The synthesis also features a mild decarbomethoxylation reaction.