Tetrahedron

Synthesis of 7-Fluoro-2, 4-methylene-17, 20-dimethylprostacyclins. Novel stable prostacyclin analogs as potent anti-anginal agents

Y Matsumura, T Shimada, T Nakayama, M Urushihara…

Index: Matsumura, Yasushi; Shimada, Toyomichi; Nakayama, Toshiaki; Urushihara, Masahiro; Asai, Tomoyuki; et al. Tetrahedron, 1995 , vol. 51, # 32 p. 8771 - 8782

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Citation Number: 24

Abstract

Synthesis of new stable fluoroprostacyclins, 7-fluoro-2, 4-methylene-17, 20- dimethylprostacyclins (1, 2) with potent and long-lasting anti-anginal activities has been achieved. The cyclobutylene prostaglandin skeleton 10 was constructed efficiently according to three-component coupling reaction. Stereospecific fluorination of silyl ether 11 and subsequent cyclization of the fluoride 12 successfully provided the desired 7-fluoro-2, ...