55(PB1-4) 海産プロスタノイドの合成研究(ポスター発表の部)

概要

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Clavulones, chlorovulones, and punaglandins are novel marine prostanoids and exhibit antitumor and antiinflammatory activity. We present here a simple and efficient route to these prostanoids which includes the following three features: (1) Enantioselective synthesis of the C_1-C_7 fragment (α-side chain) of clavulones was achieved by employing chiral sulfoxide directed reduction of a β-ketosulfoxide system under chelation control. (2) (R)-3-Chloro-4-hydroxy-2-cyclopentenone, the common starting material for 10-chlorinated marine prostanoids, was easily obtained starting from (1R,4S)-4-hydroxy-2-cyclopentenyl acetate. (3) Stereoselective introduction of the ω-side chain (C_<13>-C_<20> fragment) into 4-hydroxy cyclopentenone derivatives (4), (18) could be accomplished using the carbanion species generated by treatment of 1-bromo-2-octyne with activated Zn. Thus, we could accomplish the total syntheses of clavulone II and III and chlorovulone II based on these newly developed methods. Approaches to the synthesis of punaglandins are also described.
天然有機化合物討論会の論文
1987-07-25