Total Synthesis and Structure-Activity Investigation of the Marine Natural Product Neopeltolide

被引：79

作者：

Custar, Daniel W. ^{[1
]}

Zabawa, Thomas P. ^{[1
]}

Hines, John ^{[2
,3
]}

Crews, Craig M. ^{[2
,3
]}

Scheidt, Karl A. ^{[1
]}

机构：

[1] Northwestern Univ, Dept Chem, Ctr Mol Innovat & Drug Discovery, Evanston, IL 60208 USA

[2] Yale Univ, Dept Mol Cellular & Dev Biol, Dept Chem, New Haven, CT 06520 USA

[3] Yale Univ, Dept Pharmacol, New Haven, CT 06520 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 34期

关键词：

LEUCASCANDROLIDE-A; PRINS-CYCLIZATION; LYNGBYALOSIDE-B; ALDOL REACTION; MACROLIDE; ALDEHYDES; ALCOHOLS; ESTERS; ACIDS; STEREOCHEMISTRY;

D O I：

10.1021/ja904604x

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The total synthesis and biological evaluation of neopeltolide and analogs are reported. The key bond-forming step utilizes a Lewis acid-catalyzed intramolecular macrocyclization that installs the tetrahydropyran ring and macrocycle simultaneously. Independent of each other, neither the macrolide nor the oxazole side chain substituents of neopeltolide can inhibit the growth of cancer cell lines. The biological data of the analogs indicate that alterations to either the ester side chain or the stereochemistry of the macrolide result in a loss of biological activity.

引用

页码：12406 / 12414

页数：9

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