The synthesis of PGF₁α by re-structuring of castor oil

Abstract

Castor oil has been transformed-via methyl ricinoleate-to PGF₁α by strategy wherein 16 of the 18 carbons of the castor oil backbone are incorporated in the C-20 PGF₁α, involving, inter alia, a novel procedure for the regiospecific functionalisation of terminal olefins, a novel degradation of aldehyde to lower acid and strategies useful for the generation of the highly functionalised prostanoid system, which specially illustrate the utility of MEM protecting group in diverse types of chemical transformations. Additionally, this work describes the preparation of synthons having potential utility and the synthesis of novel homo-PGP₁α.