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
收藏
页码：1877 / 1880
页数：4
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