Stereochemical assignment of the C1-C6 fragment of psymberin by synthesis and natural product degradation

被引：33

作者：

Green, ME ^{[1
]}

Rech, JC ^{[1
]}

Floreancig, PE ^{[1
]}

机构：

[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 19期

关键词：

D O I：

10.1021/ol051396s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Psymberin is a sponge-derived natural product that shows striking selectivity as a cytotoxic agent. Conformational mobility has precluded stereochemical assignment for the acyl fragment of this molecule (psymberic acid) by NMR. Herein we report stereoselective syntheses of all four stereoisomers of psymberic acid. A comparison of the acid-mediated cyclization products of these compounds to the product of psymberin's acidic methanolysis showed the stereochemical configuration of this fragment to be 4S, 5S.

引用

页码：4117 / 4120

页数：4

共 17 条

[1] Psymberin, a potent sponge-derived cytotoxin from Psammocinia distantly related to the pederin family [J].