A Short Synthesis of Enantiomeric Phytoprostanes B₁ Type I

Abstract

The synthesis of both enantiomers of phytoprostane B₁ type I from 3-[(dimethoxyphosphoryl)methyl]cyclopent-2-enone is reported. It consists of three steps including regioselective alkylation of the substrate at C(2) with methyl 8-bromooctanoate, subsequent Horner reaction with enantiomeric O-benzoyl-protected α-hydroxybutanals and final methanolysis. This affords the product in 25% overall yield.

Key words

phytoprostanes - cyclopentenone phosphonates - alkylation - Horner alkenation - total synthesis

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