ENANTIOSELECTIVE SYNTHESIS OF 5-LO INHIBITORS USING A GULOFURANOSE AUXILIARY

被引：35

作者：

ROHLOFF, JC

ALFREDSON, TV

SCHWARTZ, MA

机构：

[1] SYNTEX INC,DISCOVERY RES,INST ANALYT RES,PALO ALTO,CA 94303

[2] FLORIDA STATE UNIV,DEPT CHEM,TALLAHASSEE,FL 32306

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 07期

关键词：

D O I：

10.1016/S0040-4039(00)79952-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The pure R-(+)-enantiomer of 5-lipoxygenase inhibitor Zileuton was prepared by diastereoselective methyl Grignard addition to an aldonitrone bearing a D-gulofuranose-derived chiral auxiliary. Addition of the Lewis acid trimethylaluminum leads to a reversal of the alkylation stereochemistry and the potent pyrido analogue, R-(+)-RS-27871 was prepared in this way from an L-gulofuranose-derived nitrone.

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页码：1011 / 1014

页数：4

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