串联 Prins/Schmidt 反应方法在海洋生物碱中的应用：Lepadiformines A 和 C 的形式和全合成。
A tandem Prins/Schmidt reaction approach to marine alkaloids: formal and total syntheses of lepadiformines A and C.
机构信息
Department of Medicinal Chemistry, University of Kansas, Structural Biology Center, 2121 Simons Drive, West Campus, Lawrence, Kansas 66047, USA.
出版信息
Org Lett. 2010 Mar 19;12(6):1244-7. doi: 10.1021/ol100113r.
Abstract
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.
摘要
生物碱天然产物的三环核心通过路易斯酸条件下的 Prins 加成/分子内施密特重排来组装。该过程的单一锅和两阶段变化都进行了研究，特别关注了过程的立体化学结果。该技术已应用于 Lepadiformine A 的正式全合成和 Lepadiformine C 的全合成。
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