海兔毒素N7-C25片段的简洁立体选择性合成。

Concise and stereoselective synthesis of the N7-C25 fragment of psymberin.

作者信息

Rech Jason C, Floreancig Paul E

机构信息

Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.

出版信息

Org Lett. 2005 Nov 10;7(23):5175-8. doi: 10.1021/ol0520267.

DOI:10.1021/ol0520267

PMID:16268531

Abstract

[reaction: see text] The N7-C25 fragment of the potent and selective cytotoxic agent psymberin has been prepared through a short (12 linear steps, 15 total steps) and stereoselective sequence. Highlights of this route include a very rapid construction of the pentasubstituted arene, a substrate-controlled diastereoselective fragment coupling using a Mukaiyama aldol reaction, and an efficient entry into a key tetrahydropyranyl cyanide.

摘要

[反应：见正文] 强效选择性细胞毒性剂psymberin的N7-C25片段已通过一条简短的（12步线性步骤，共15步）立体选择性合成路线制备而成。该路线的亮点包括非常快速地构建五取代芳烃、使用木山羟醛反应进行底物控制的非对映选择性片段偶联以及高效合成关键的四氢吡喃基氰化物。