A Short Synthesis of Enantiomeric Phytoprostanes B1 Type I
Synthesis
DOI: 10.1055/s-0029-1216883
Abstract
The synthesis of both enantiomers of phytoprostane B 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.
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© Georg Thieme Verlag Stuttgart ˙ New York
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