Synthesis of (±)-recifeiolide
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A description is given of the directed synthesis of (±)-recifeiolide (VI), starting from cyclooctene and 1-chlorobutan-3-ol. The ozonolysis of cyclooctene gave 7-for-mylheptanoic acid, the methyl ester of which (II) was condensed with the ylide of (3-hydroxybut-1-yl) triphenylphosphonium iodide (I) synthesized from 1-chlorobutan-3-ol. The lactonization of the 11-hydroxydodec-8(E)-enoic acid so obtained gave (VI). The IR, PMR, and mass spectra of (VI) are presented.
KeywordsCoumarin Cyclooctene Phosphonium Salt Anhydrous Benzene Enoic Acid
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- 5.K. Narasaka, M. Yamaguchi, and T. Mikaiyama, Chem. Lett.,959 (1977).Google Scholar