Journal of Organic Chemistry 2000-08-25

A novel synthesis of racemic and enantiomeric forms of prostaglandin B1 methyl ester.

M Mikołajczyk, M Mikina, A Jankowiak

Index: J. Org. Chem. 65(17) , 5127-30, (2000)

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Abstract

3-(Dimethoxyphosphorylmethyl)cyclopent-2-enone was converted into (+/-)-prostaglandin B1 methyl ester in two steps involving regioselective alkylation at C(2) with methyl 7-iodoheptanoate and subsequent Horner-Wittig reaction with dimer of 2-hydroxyheptanal (42% overall yield). The use of (R)- and (S)-2-(tert-butyldimethylsilyloxy)heptanal for the Horner olefination reaction gave, after deprotection of the hydroxy group, the enantiopure forms of the title compound in 28% overall yield.