Total Synthesis of Ustiloxin D Utilizing an Ammonia-Ugi Reaction

被引：23
作者：
Brown, Aaron L.
Churches, Quentin I.
Hutton, Craig A. [1 ]
机构：
[1] Univ Melbourne, Sch Chem, Parkville, Vic 3010, Australia
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 20期
基金：
澳大利亚研究理事会;
关键词：
FALSE SMUT BALLS; MULTICOMPONENT REACTIONS; NATURAL-PRODUCTS; 4-COMPONENT; SELECTIVITY;
D O I：
10.1021/acs.joc.5b01519
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Total synthesis of the highly functionalized cyclic peptide natural product, ustiloxin D, has been achieved in a convergent manner. Our strategy incorporates an asymmetric allylic alkylation to construct the tert-alkyl aryl ether linkage between the dopa and isoleucine residues. The elaborated beta-hydroxydopa derivative is rapidly converted to a linear tripeptide through an ammonia-Ugi reaction. Subsequent cyclization and global deprotection affords ustiloxin D in six steps from a known beta-hydroxydopa derivative.
引用
收藏
页码：9831 / 9837
页数：7
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