Syntheses of (5E)-PGE2 and new 6-functionalized derivatives by the use of palladium-catalyzed decarboxylative allylic alkylation

T Tanaka, N Okamura, K Bannai, A Hazato, S Sugiura…

Index: Tanaka, Toshio; Okamura, Noriaki; Bannai, Kiyoshi; Hazato, Atsuo; Sugiura, Satoshi; et al. Tetrahedron, 1986 , vol. 42, # 24 p. 6747 - 6758

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Citation Number: 16

Abstract

(5E)-Prostaglandin E2 (7) was synthesized fron (R)-4-t-butyldimethylsilyloxy-2- cyclopentenone (1) by in situ 2-alkenyloxycarbonylatlon of the organocopper conjugate- addition adduct (3) followed by intramolecular palladium-catalyzed decarboxylative allylic alkylation. The (5E)-prostaglandin E2 skeleton was also obtained from the β-keto allylic ester (11) by a similar decarboxylative allylic alkylation. The decarboxylative allylic ...