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■ Synthesis of Scyphostatin Analogs Possessing Various Saturated Fatty Acid Side-Chains

Kazuhiro Watanabe, Takamasa Oguchi, Toshiya Takizawa, Miki Furuuchi, Hideki Abe, and Tadashi Katoh*

*Laboratory of Synthetic Medicinal Chemistry, Department of Chemical Pharmaceutical Science, Tohoku Pharmaceutical University, Komatsushima, Aoba-ku, Sendai 981-8558, Japan

Abstract

Scyphostatin analogs 2a-f possessing various saturated fatty acid side-chains (C₁₂-C₁₉) were efficiently synthesized in enantiomerically pure form starting from the known cyclohexene derivative 3. These analogs were designed to improve the stability of scyphostatin (1), a powerful and specific inhibitor of neutral sphingomyelinase (N-SMase) from a microorganism.