Rapid synthesis of the 7-deoxy zaragozic acid core

被引：57

作者：

Calter, MA ^{[1
]}

Zhu, C ^{[1
]}

Lachicotte, RJ ^{[1
]}

机构：

[1] Univ Rochester, Dept Chem, Rochester, NY 14627 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 02期

关键词：

D O I：

10.1021/ol0169980

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] We have developed an efficient synthesis of the 7-deoxy zaragozic acid core. The synthesis begins with a Feist-Benary reaction that assembles all three carbons of the polycarboxylic acid portion of the core. This reaction is followed by highly diastereoselective aldol and dihydroxylation reactions that set the remaining stereocenters of the core. The synthesis finishes with lactol oxidation and lactone alcoholysis/ketal formation reactions to construct the bicyclic ring system of the core.

引用

页码：209 / 212

页数：4

共 10 条

[1] THE SQUALESTATINS, NOVEL INHIBITORS OF SQUALENE SYNTHASE PRODUCED BY A SPECIES OF PHOMA .5. MINOR METABOLITES [J].