Total Synthesis of (-)-Nodulisporic Acids D, C, and B: Evolution of a Unified Synthetic Strategy

被引：27

作者：

Zou, Yike

Li, Xiangqin

Yang, Yun

Berritt, Simon

Melvin, Jason

Gonzales, Stephen

Spafford, Matthew

Smith, Amos B., III ^{[1
]}

机构：

[1] Univ Penn, Dept Chem, Res Struct Matter Lab, Philadelphia, PA 19104 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2018年 / 140卷 / 30期

基金：

美国国家卫生研究院;

关键词：

PALLADIUM-CATALYZED CONVERSION; MIYAURA COUPLING REACTIONS; NODULISPORIC ACID; ASYMMETRIC-SYNTHESIS; CARBONYL ADDITION; ALLYL HALIDES; CONSTRUCTION; ALKYLATION; REAGENTS; ARYL;

D O I：

10.1021/jacs.8b04053

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A unified synthetic strategy leading to the total synthesis of (-)-nodulisporic acids D, C, and B is described. Key synthetic transformations include a nickel-chromium-mediated cyclization, an aromatic ring functionalization employing a novel copper-promoted alkylation, a palladium-catalyzed cross-coupling cascade/indole ring construction, and a palladium-mediated regio- and diastereoselective allylic substitution/cyclization reaction, the latter to construct ring D.

引用

页码：9502 / 9511

页数：10

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