Coupling reaction of 4-cyclopentene-1,3-diol monoacetate and lithium alkenylborates and its application to chiral synthesis of prostaglandin intermediates

被引：35

作者：

Usmani, SB ^{[1
]}

Takahisa, E ^{[1
]}

Kobayashi, Y ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Biomol Engn, Midori Ku, Yokohama, Kanagawa 226, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 07期

关键词：

D O I：

10.1016/S0040-4039(97)10655-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lithium alkenylborates couple with the monoacetate of 4-cyclopentene-1,3-diol under the nickel catalyst regioselectively and stereospecifically to afford trans 1,3-isomers in good yields. Moreover, an unexpectedly high level of regio-selectivity is observed with the alkenylborates possessing the prostaglandin (PG) omega-chain structure. The present reaction is successfully applied to the asymmetric synthesis of PG intermediates 9, 15, 16. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：601 / 604

页数：4

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