合成瓜环烷生物碱哌啶环全部非对映异构体。

Synthesis of all diastereomers of the piperidine--alkaloid substructure of cyclopamine.

机构信息

Institut für Organische Chemie, Universität Leipzig, 04103 Leipzig, Germany.

出版信息

Org Lett. 2009 Dec 3;11(23):5410-2. doi: 10.1021/ol902270f.

PMID:19883099

Abstract

All four diastereomers of the trisubstituted piperidine-alkaloids of the veratramine and jervine type were synthesized with complete stereocontrol starting from enantiopure citronellic acids. The flexible, high-yielding, and scalable route described here will facilitate convergent syntheses and give access to analogues of cyclopamine and other biologically active and diverse steroid alkaloids.

摘要

所有四个立体异构体的三取代哌啶型藜芦碱和金雀花碱型都是从手性纯香茅酸出发，通过完全立体控制合成的。这里描述的灵活、高产和可扩展的路线将促进收敛合成，并获得类似环巴胺和其他生物活性和多样的甾体生物碱的类似物。