Synthesis of (E, Z)-5-bromo-1, 1-dimethoxy-5-trimethylsilyl-4-pentene, an upper chain allenic prostaglandin building block

A Guzmán-Durán, E Guzmán, KH Pannell…

Index: Guzman-Duran, Antonio; Guzman, Esther; Pannell, Keith H.; Lloyd, Winston D. Synthetic Communications, 2003 , vol. 33, # 19 p. 3271 - 3283

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Citation Number: 4

Abstract

Abstract This work explores the synthetic route to allenic prostaglandins. In a search for more efficient and reliable methods for the introduction of the allene moiety into the side chains of prostaglandins, the synthons, the (E) and (Z) isomers of 1-bromo-5, 5-dimethoxy-1- trimethylsilyl-1-pentene (13a) and (13b), have been prepared and converted to R, S-1, 1- dimethoxy-6-phenyl-4, 5-hexadiene (16), a prostaglandin analog.