Highly efficient total synthesis of Δ 12-PGJ 2, 15-deoxy-Δ 12, 14-PGJ 2, and their analogues

HP Acharya, Y Kobayashi

Index: Acharya, Hukum P.; Kobayashi, Yuichi Tetrahedron, 2006 , vol. 62, # 14 p. 3329 - 3343

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Citation Number: 36

Abstract

Palladium-catalyzed reaction of TBS ether of 4-cyclopentene-1, 3-diol monoacetate (> 95% ee) with an anion derived from methyl malonate and a base such as t-BuOK and LDA proceeded highly efficiently and reproducibly. The product obtained in> 90% isolated yield was transformed in five steps into the key cyclopentenone possessing the α-chain at the γ position. Aldol reaction of this enone with the ω-chain aldehyde afforded the aldol adduct, ...