通过非稳定甲亚胺叶立德的分子内1,3-偶极环加成反应合成5,11-甲撑吗啡烷类生物碱的立体专一性路线：(±)- pancracine的形式全合成。

Stereospecific route to 5,11-methanomorphanthridine alkaloids via intramolecular 1,3-dipolar cycloaddition of nonstabilized azomethine ylide: formal total synthesis of (+/-)-pancracine.

作者信息

Pandey Ganesh, Banerjee Prabal, Kumar Ravindra, Puranik Vedavati G

机构信息

Division of Organic Chemistry (Synthesis) and Center for Material Characterization, National Chemical Laboratory, Pune 411008, India.

出版信息

Org Lett. 2005 Aug 18;7(17):3713-6. doi: 10.1021/ol051321o.

DOI:10.1021/ol051321o

PMID:16092857

Abstract

The core structure of the complex pentacyclic 5,11-methanomorphanthridine alkaloids is constructed stereospecifically in one step employing an intramolecular [3 + 2]-cycloaddition of nonstabilized azomethine ylide as the key step. The strategy is demonstrated by accomplishing the formal total synthesis of (+/-)-pancracine. [reaction: see text]

摘要

复杂的五环5,11-亚甲基吗啡烷类生物碱的核心结构通过一步立体专一性构建而成，该步骤采用非稳定甲亚胺叶立德的分子内[3+2]环加成反应作为关键步骤。通过完成(±)-水仙环素的形式全合成证明了该策略。[反应：见正文]