Tetrahedron

Synthesis of 5, 6, 7-Trinor-4, 8-inter-m-phenylene PGI 2 and Beraprost

…, K Matsumoto, H Yoshiwara, Y Hosono, R Hayashi…

Index: Wakita, Hisanori; Matsumoto, Kazuhisa; Yoshiwara, Hideo; Hosono, Yutaka; Hayashi, Ryoji; Nishiyama, Hisao; Nagase, Hiroshi Tetrahedron, 1999 , vol. 55, # 9 p. 2449 - 2474

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Citation Number: 23

Abstract

We have disclosed a new class of stable PGI2 analogue, 5, 6, 7-trinor-4, 8-inter-m- phenylene PGI2 which has a phenyl ether moiety instead of enol-ether skeleton in PGI2. The m-phenylene PGI2 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 ω-side ...