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■ Synthesis of 14,15-Epoxyisoprostane A₂ Phosphorylcholine

Hukum P. Acharya, Kei Miyoshi, Yuji Takashima, Narihito Ogawa, and Yuichi Kobayashi*

*Department of Biomolecular Engineering, Tokyo Institute of Technology, B52, Nagatsuta-cho 4259, Midori-ku, Yokohama 226-8501, Japan

Abstract

The product of the copper-promoted allylic substitution of the 4-hydroxycyclopent-2-enyl ester with TMS-C≡CCH₂MgBr was converted to the cyclopentenone with the PMBO(CH₂)₄CH=CHCH₂ side chain. Aldol reaction of the enone with the epoxy aldehyde derived from (E)-oct-2-en-1-ol through the Sharpless asymmetric epoxidation gave the full structure of the isoprostane. Dehydration, conversion of the PMBOCH₂ moiety to CO₂H, and condensation with lysophosphorylcholine produced the title molecule.