Total Synthesis of Seongsanamide B

被引:15
作者
Shabani, Sadegh [1 ,2 ]
Hutton, Craig A. [1 ,2 ]
机构
[1] Univ Melbourne, Sch Chem, Melbourne, Vic 3010, Australia
[2] Univ Melbourne, Bio21 Mol Sci & Biotechnol Inst, Melbourne, Vic 3010, Australia
基金
澳大利亚研究理事会;
关键词
INTRAMOLECULAR O-ARYLATION; ENANTIOSELECTIVE SYNTHESIS; ISODITYROSINE; PEPTIDES; K-13; (S; S)-ISODITYROSINE; MACROLACTAMIZATION; MACROCYCLIZATION; DITYROSINE; OF4949-III;
D O I
10.1021/acs.orglett.0c01642
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first total synthesis of the bicyclic depsipeptide natural product seongsanamide B is described. The successful approach employed solid-phase peptide synthesis of a core heptapeptide, incorporating on-resin esterification, followed by solutionphase macrolactamization and a late stage intramolecular Evans-Chan-Lam coupling to generate the biaryl ether of the isodityrosine unit.
引用
收藏
页码:4557 / 4561
页数:5
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