外螯菌素MN及其类似物的全合成。

Total synthesis of exochelin MN and analogues.

作者信息

Dong Li, Miller Marvin J

机构信息

Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, Indiana 46556-5670, USA.

出版信息

J Org Chem. 2002 Jul 12;67(14):4759-70. doi: 10.1021/jo0256078.

DOI:10.1021/jo0256078

PMID:12098286

Abstract

The first total synthesis of exochelin MN is described along with rationally designed analogues. The required L-threo-beta-hydroxyamino acid components were constructed using either Sharpless asymmetric aminohydroxylation reactions or an aldol reaction of imidazolidinone 19. A new concise procedure for the preparation of the constituent six-membered cyclic hydroxamate was developed. In addition, a plausible mechanism for exochelin MN-mediated iron(III) transport was proposed. Biological studies of these compounds will be used to evaluate this hypothesis.

摘要

本文描述了外螯菌素MN的首次全合成及其合理设计的类似物。所需的L-苏式-β-羟基氨基酸组分通过Sharpless不对称氨基羟基化反应或咪唑烷酮19的羟醛反应构建。开发了一种制备组成性六元环异羟肟酸酯的新的简洁方法。此外，还提出了外螯菌素MN介导铁(III)转运的合理机制。这些化合物的生物学研究将用于评估这一假设。