Three-component coupling synthesis of prostaglandins: The aldol route.

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概要

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• A one-pot, high yield construction of the whole prostaglandin (PG) skeleton is accomplishable by combination of the copper-mediated conjugate addition of an ω side-chain unit to a 4<I>R</I>-oxygenated 2-cyclopentenone derivative and aldol condensation of the in situ generated enolate with an α side-chain aldehyde. Subsequent removal of the 7-hydroxyl group from the adducts and deblocking of the protective groups give PGs of E series. PGE<SUB>1</SUB> has been prepared in 56% overall yield through the five-step sequence. Selective transformation of the PGE to PGD structure can be realized simply by appropriate selection of the hydroxyl protective groups in the five-membered ring and ω side-chain units. The vicinal carba-condensation using methyl 6-formyl-5-hexynoate as the α side-chain aldehyde unit followed by deoxygenation from the aldol products gives the 5,6-didehydro-PGE<SUB>2</SUB> derivatives which serve as key intermediates in the general synthesis of various natural PGs. An efficient method for resolution of 4-hydroxy-2-cyclopentenone is also described.

• 公益社団法人 日本化学会の論文

著者

• Suzuki Masaaki

  Department Of Atherosclerosis Metabolism And Clinical Nutrition National Cardiovascular Center

• Noyori Ryoji

  Department Of Chemistry And Molecular Chirality Research Unit Nagoya University

• Yanagisawa Akira

  Department Of Applied Chemistry National Defense Academy

• Suzuki Masaaki

  Department of Chemistry, Nagoya University

• Suzuki Takehiko

  Department of Chemistry, Nagoya University

• Kawagishi Toshio

  Department of Chemistry, Nagoya University

• Okamura Noriaki

  Department of Chemistry, Nagoya University

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