Triply convergent synthesis of 15-(phenoxymethyl) and 4, 5-allenyl prostaglandins. Preparation of an individual isomer of enprostil

OW Gooding, CC Beard, GF Cooper…

Index: Gooding, Owen W.; Beard, Colin C.; Cooper, Gary F.; Jackson, David Y. Journal of Organic Chemistry, 1993 , vol. 58, # 14 p. 3681 - 3686

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Citation Number: 27

Abstract

A triply convergent synthesis of the PGEz derivatives 1, 3, 4, and 5, containing either the 15- (phenoxymethyl) or the 15-amyl w side chain and the 5, 6-didehydro or the 4, 5-allenyl a side chain, is described. This two-pot method employs organocopper reagents of the type LizRJJuCNMe to selectively introduce the w side chain to enantiopure enone 6 followed by in situ trapping of the so-formed enolates as silyl enol ethers 22a and 22b. The key step is ...