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
收藏
页码：602 / 605
页数：4
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