Tetrahedron

Stereospecific nitromethane conjugate addition to 4-oxygenated-2-substituted-cyclo pent-2-enones: a simple approach to prostaglandins

PG Baraldi, A Barco, S Benetti, GP Pollini, D Simoni…

Index: Baraldi, P. G.; Barco, A.; Benetti, S.; Pollini, G. P.; Simoni, D.; Zanirato, V. Tetrahedron, 1987 , vol. 43, # 20 p. 4669 - 4678

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Citation Number: 14

Abstract

The compatibility of nitromethane conjugate addition to 2-cyclo-pentenones bearing a 4- oxygenated function has been illustrated through a short and practical synthesis of the Corey aldehyde, a key intermediate in prostaglandin synthesis, in both racemic and optically active form. A new synthesis of PGF2α featuring the introduction of the ω-chain via [3+ 2] cycloaddition has been also described.