An Efficient Synthesis of (?)-Lycoricidine Featuring a Stille-IMDAF Cycloaddition Cascade

• Authors: Hongjun Zhang, Emory University; Albert Padwa, Emory University
• Journal Title: Organic Letters
• Volume: Volume 8, Number 2
• Publisher: American Chemical Society | 2006-01-19, Pages 247-250
• Type of Work: Article | Post-print: After Peer Review
• Publisher DOI: http://doi.org/10.1021/ol052524f
• Subjects: Chemistry, Organic

Abstract

A highly efficient total synthesis of (±)-Lycoricidine is described. The synthesis features the ready preparation of the lycoricidine skeleton by a Stille-IMDAF cycloaddition cascade. The resulting cycloadduct is then used for the stereocontrolled installation of the other functionality present in the C-ring of the target molecule.