A convenient and asymmetric protocol for the synthesis of natural products containing chiral alkyl chains via Zr-catalyzed asymmetric carboalumination of alkenes. Synthesis of phytol and vitamins E and K

被引：60

作者：

Huo, SQ ^{[1
]}

Negishi, EI ^{[1
]}

机构：

[1] Purdue Univ, HC Brown & RB Wetherill Labs Chem, W Lafayette, IN 47907 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 21期

关键词：

D O I：

10.1021/ol010142d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A convenient and asymmetric protocol for the synthesis of chiral oligoisoprenoids is described. Typically, a C-14 vitamin E side chain 5 was synthesized in 47% yield over four steps. Isomeric purity of 5 was upgraded to > 99% R at C-2 and 97% R at C-6 by the statistical formation of stereoisomeric p-phenylenebisurethanes and their diastereomeric separation. In addition, phytol and vitamin K were synthesized in 21% and 28% overall yields, respectively, over five steps from 1.

引用

页码：3253 / 3256

页数：4

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