Diastereoselective synthesis of the 5-hydroxy-pyrrolidinone amino acid of the microsclerodermins and model studies for an end-game strategy for microsclerodermin B

被引：3

作者：

Winter, Christian ^{[1
]}

Pullin, Robert D. C. ^{[1
]}

Donohoe, Timothy J. ^{[1
]}

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, Mansfield Rd, Oxford OX1 3TA, England

来源：

TETRAHEDRON LETTERS | 2017年 / 58卷 / 07期

基金：

英国工程与自然科学研究理事会;

关键词：

Amino acids; Cyclic peptides; Stereoselective synthesis; Peptide coupling; Metathesis; ANTIFUNGAL CYCLIC-PEPTIDES; STEREOSELECTIVE-SYNTHESIS; F-I; MYXOBACTERIA; CONSTITUENTS; AMMTD; AETD; CORE; APTO;

D O I：

10.1016/j.tetlet.2016.12.045

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first diastereoselective synthesis of the 5-hydroxy-pyrrolidinone amino acid common to eight members of the microsclerodermin family is presented. Our strategy involves formal hydration of an unsaturated precursor via the use of a two-step hydroxybromination-debromination protocol; this procedure provides exclusively the requisite 4,5-cis-pyrrolidinone. Furthermore model studies are presented that indicated the potential viability of this hydration strategy in the context of a synthesis of microsclerodermin B. (C) 2016 The Authors. Published by Elsevier Ltd.

引用

页码：602 / 605

页数：4

共 22 条

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