A Tandem Prins/Schmidt Reaction Approach to Marine Alkaloids: Formal and Total Syntheses of Lepadiformines A and C

作者:Meyer Angelica M; Katz Christopher E; Li Sze Wan; Velde David Vander; Aube Jeffrey*
来源:Organic Letters, 2010, 12(6): 1244-1247.
DOI:10.1021/ol100113r

摘要

The tricyclic core of the cylindricine or lepadiformine families of alkaloid natural products was assembled via a Prins addition/intramolecular Schmidt rearrangement under Lewis acid conditions. Both single-pot and two-stage variations of this process were examined, with particular attention to the stereochemical outcome of the processes. This technology has been applied to a formal total synthesis of lepadiformine A and a total synthesis of lepadiformine C.

  • 出版日期2010-3-19