Synthesis of the C-Terminal Macrocycle of Asperipin-2a

被引：5

作者：

Shabani, Sadegh ^{[1
,2
]}

White, Jonathan M. ^{[1
,2
]}

Hutton, Craig A. ^{[1
,2
]}

机构：

[1] Univ Melbourne, Sch Chem, Melbourne, Vic 3010, Australia

[2] Univ Melbourne, Mol Sci & Biotechnol Inst Bio21, Melbourne, Vic 3010, Australia

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 06期

基金：

澳大利亚研究理事会;

关键词：

ANTIMITOTIC CYCLIC-PEPTIDES; FALSE SMUT BALLS; NATURAL-PRODUCTS; USTILOXIN B; LEWIS-ACID; AZIRIDINE; TRYPTOPHAN; PHENYLALANINE; CYCLIZATION;

D O I：

10.1021/acs.orglett.9b00488

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthetic approach to the C-terminal macrocycle of asperipin-2a is presented. Two epimers were prepared, possessing R- and S-configurations at the beta-position of Tyr(3). Comparison of NMR data of the natural product with these isomers and X-ray crystallographic data for one macrocycle support assignment of the 2S,3S-configuration of Tyr(3). Key steps in the synthesis include a stereoselective benzylic oxidation of the tyrosine residue and Lewis-acid-catalyzed ring opening of the subsequently generated aziridine.

引用

页码：1877 / 1880

页数：4

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