Synthesis 2009(16): 2715-2718  
DOI: 10.1055/s-0029-1216883
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Short Synthesis of Enantiomeric Phytoprostanes B1 Type I

Wiesława Perlikowska, Marian Mikołajczyk*
Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Department of Heteroorganic Chemistry, Sienkiewicza 112, 90-363 Łódż, Poland
e-Mail: marmikol@bilbo.cbmm.lodz.pl;
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Publikationsverlauf

Received 26 February 2009
Publikationsdatum:
01. Juli 2009 (online)

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.