Stereoselective Synthesis of (+)-Polyoxamic Acid Starting with a Chiral Aziridine

被引：3

作者：

Yoon, Hojong ^{[1
]}

Sim, Taebo ^{[1
,2
]}

机构：

[1] Korea Inst Sci & Technol, Chem Kin Res Ctr, Seoul 136791, South Korea

[2] KU KIST Grad Sch Converging Sci & Technol, Seoul 136713, South Korea

来源：

SYNTHESIS-STUTTGART | 2013年 / 45卷 / 23期

基金：

新加坡国家研究基金会;

关键词：

polyhydroxylated amino acid; (+)-polyoxamic acid; natural product synthesis; chiral aziridine; asymmetric dihydroxylation; ALPHA-AMINO-ACIDS; POLYOXAMIC ACID; ASYMMETRIC-SYNTHESIS; EFFICIENT SYNTHESIS; REARRANGEMENT; ANTIBIOTICS; DERIVATIVES; POLYOXINS;

D O I：

10.1055/s-0033-1338545

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and stereoselective synthesis of (+)-polyoxamic acid was developed. The route starts with the commercially available 1-(R)--methylbenzylaziridine-2-methanol, a substance that has not been used previously as a starting material for the preparation of this target. The route also features the use of a stereocontrolled Sharpless asymmetric dihydroxylation reaction, promoted by AD-mix-, which is followed by a regioselective aziridine ring-opening process, to generate the basic skeleton of target natural product. Subsequent oxidation and global deprotection produces (+)-polyoxamic acid.

引用

页码：3276 / 3280

页数：5

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