Enantioselective Synthesis of Both Epimers at C-21 in the Proposed Structure of Cytotoxic Macrolide Callyspongiolide

被引：19

作者：

Ghosh, Arun K. ^{[1
]}

Kassekert, Luke A.

机构：

[1] Purdue Univ, Dept Chem, 560 Oval Dr, W Lafayette, IN 47907 USA

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 13期

基金：

美国国家卫生研究院;

关键词：

MARINE SPONGE; (-)-LAULIMALIDE; POLYKETIDE; REDUCTION; ALDEHYDES; SULFONES; KETONES;

D O I：

10.1021/acs.orglett.6b01523

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Both epimers at C-21 in the proposed structure of (+)-call-yspongiolide have been synthesized in a convergent and enantioselective manner. The 14-membered macrolide with a sensitive C2-C3 cis-olefin functionality was installed by a Yamaguchi macrolactonization of hydroxyl alkynoic acid followed by hydrogenation over Lindlar's catalyst. The CS methyl stereocenter was constructed by a ring-dosing olefin metathesis followed by addition of methyl cuprate to an alpha,beta-unsaturated delta-lactone. Other key reactions are chiral Corey-Bakshi Shibata (CBS) reduction and Sonogashira coupling to conjoin the macrocyclic core and side chain.

引用

页码：3274 / 3277

页数：4