Development of a Merged Conjugate Addition/Oxidative Coupling Sequence. Application to the Enantioselective Total Synthesis of Metacycloprodigiosin and Prodigiosin R1

被引：74

作者：

Clift, Michael D. ^{[1
]}

Thomson, Regan J. ^{[1
]}

机构：

[1] Northwestern Univ, Dept Chem, Evanston, IL 60208 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 40期

关键词：

CARBON BOND FORMATION; TRIMETHYLSILYL ENOL ETHERS; FRIEDEL-CRAFTS ALKYLATION; MUKAIYAMA ALDOL REACTION; DILITHIOMETHANE EQUIVALENT; BACTERIAL PRODIGININES; 1,4-DIKETONES; ENONES; ROSEOPHILIN; ANTICANCER;

D O I：

10.1021/ja906122g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A merged conjugate addition/oxidative coupling sequence that represents an efficient strategy for preparing structurally diverse pyrroles has been developed. Success of the method hinged upon the controlled oxidative coupling of unsymmetrical silyl bis-enol ether intermediates, formed by the 1,4-addition of a Grignard reagent with subsequent enolate trapping by a (chloro)silylenol ether. The process was applied to the first enantioselective syntheses of the biologically active pyrrolophane natural products, metacycloprodigiosin and prodigiosin R1.

引用

页码：14579 / 14583

页数：5

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