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Paper | Special issue | Vol 76, No. 2, 2008, pp.1181-1189
Published online, 30th June, 2008
DOI: 10.3987/COM-08-S(N)78
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


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.