A catalytic asymmetric synthesis of 11-deoxy-PGF1α, using ALB, a heterobimetallic multifunctional asymmetric complex

被引：77

作者：

Yamada, K ^{[1
]}

Arai, T ^{[1
]}

Sasai, H ^{[1
]}

Shibasaki, M ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 113, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 11期

关键词：

D O I：

10.1021/jo9723319

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A catalytic asymmetric synthesis of 11-deoxy-PGF(1 alpha) has been achieved using a cascade Michael-aldol reaction as a key step. This cascade reaction was efficiently promoted by a catalytic use of AlLibis[(S)-binaphthoxide] complex (ALB) to give the three-component coupling product at room temperature in 92% ee and in 84% yield. The three-component coupling product was then converted to (+)-11-deoxy-PGF(1 alpha) through several steps, including an oxidative decarboxylation, an aldol reaction, and a Wharton reaction. Moreover, the racemic enone, 20 was transformed into 21, the three-component coupling product, a potential intermediate for PGF(1 alpha), in 97% ee and in 75% yield through catalytic kinetic resolution.

引用

页码：3666 / 3672

页数：7

共 27 条

[1]

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[2]

ALVAREZ FS, 1973, TETRAHEDRON LETT, P569

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