Total synthesis of pinnamine and anatoxin-a via a common intermediate. A caveat on the anatoxin-a endgame

T Hjelmgaard, I Søtofte, D Tanner

文献索引：Hjelmgaard, Thomas; Sotofte, Inger; Tanner, David Journal of Organic Chemistry, 2005 , vol. 70, # 14 p. 5688 - 5697

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被引用次数: 30

摘要

This paper describes the total synthesis of the naturally occurring alkaloids pinnamine (1) and anatoxin-a (2) from a common enantiomerically pure intermediate (7) easily available from pyroglutamic acid. The synthesis of enantiopure pinnamine proceeded in 10 steps and 4.8% overall yield, and the route was flexible enough to allow stereocontrolled access to a non-natural congener (5-epi-pinnamine) of the natural product. Intramolecular reaction of ...