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Synthesis 2009(16): 2715-2718
DOI: 10.1055/s-0029-1216883
DOI: 10.1055/s-0029-1216883
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
A Short Synthesis of Enantiomeric Phytoprostanes B1 Type I
Further Information
Received
26 February 2009
Publication Date:
01 July 2009 (online)
Publication History
Publication Date:
01 July 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.
Key words
phytoprostanes - cyclopentenone phosphonates - alkylation - Horner alkenation - total synthesis
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