Total synthesis of neopeltolide and analogs

被引：37

作者：

Cui, Yubo ^{[1
]}

Tu, Wangyang ^{[1
]}

Floreancig, Paul E. ^{[1
]}

机构：

[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

来源：

TETRAHEDRON | 2010年 / 66卷 / 26期

基金：

美国国家卫生研究院;

关键词：

Synthesis; Cations; Macrocycles; Oxidation; Analogs; FORMAL TOTAL-SYNTHESIS; STEREOCONTROLLED TOTAL-SYNTHESIS; ENANTIOSELECTIVE TOTAL-SYNTHESIS; BETA-HYDROXY KETONES; LEUCASCANDROLIDE-A; STEREOSELECTIVE-SYNTHESIS; (+)-LEUCASCANDROLIDE-A MACROLACTONE; INTRAMOLECULAR HYDROSILATION; MACROLIDE (+)-NEOPELTOLIDE; CYCLIZATION REACTIONS;

D O I：

10.1016/j.tet.2010.03.066

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Neopeltolide, a potent cytotoxin from a Carribean sponge, was synthesized through a brief sequence that highlights the use of ethers as oxocarbenium ion precursors. Other key steps include an acid-mediated etherification and sequence that features a Sonogashira reaction, an intramolecular alkyne hydrosilylation reaction, and a Tamao oxidation. The alkene that is required for the oxidative cyclization can be hydrogenated to provide access to the natural product or an epimer, or can be epoxiclized or dihydroxylated to form polar analogs. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：4867 / 4873

页数：7

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