Synthesis of 5,6,7-trinor-4,8-inter-m-phenylene PGI2 and Beraprost

被引：31

作者：

Wakita, H ^{[1
]}

Matsumoto, K ^{[1
]}

Yoshiwara, H ^{[1
]}

Hosono, Y ^{[1
]}

Hayashi, R ^{[1
]}

Nishiyama, H ^{[1
]}

Nagase, H ^{[1
]}

机构：

[1] Toray Ind Inc, Basic Res Labs, Kamakura, Kanagawa 2488555, Japan

来源：

TETRAHEDRON | 1999年 / 55卷 / 09期

关键词：

D O I：

10.1016/S0040-4020(99)00020-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have disclosed a new class of stable PGI(2) analogue, 5,6,7-trinor-4,8-inter-m-phenylene PGI(2) which has a phenyl ether moiety instead of enol-ether skeleton in PGI(2). The m-phenylene PGI(2) and its derivative (Beraprost) were synthesized via dihydrocyclopenta[b]benzofuran derivatives as key intermediates by ortho-selective metal-halogen exchange reaction with Grignard reagents and subsequent copper-catalyzed cyclization. The omega-side chains were introduced by stereoselective epoxide formation or Prins reaction. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：2449 / 2474

页数：26

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