Evolution of a gram-scale synthesis of (+)-discodermolide

被引：224

作者：

Smith, AB ^{[1
]}

Beauchamp, TJ

LaMarche, MJ

Kaufman, MD

Qiu, YP

Arimoto, H

Jones, DR

Kobayashi, K

机构：

[1] Univ Penn, Monell Chem Senses Ctr, Dept Chem, Philadelphia, PA 19104 USA

[2] Univ Penn, Res Struct Matter Lab, Philadelphia, PA 19104 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2000年 / 122卷 / 36期

关键词：

D O I：

10.1021/ja0015287

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient, highly convergent, stereocontrolled total synthesis of the potent antimitotic agent (+)-discodermolide (1) has been achieved on gram scale. Key elements of the successful strategy include (1) elaboration of three advanced fragments from a common precursor (CP) which embodies the repeating stereochemical triad of the discodermolide backbone, (2) a-bond installation of the Z trisubstituted olefin, exploiting a modified Negishi cross-coupling reaction, (3) synthesis of a late-stage phosphonium salt utilizing high pressure, and (4) Wittig installation of the Z disubstituted olefin and the terminal (Z)-diene.

引用

页码：8654 / 8664

页数：11

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