Abstract
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.
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Institute of Chemistry, Bashkir Branch, Academy of Sciences of the USSR, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 291–294, May–June, 1982.
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Miftakhov, M.S., Akbutina, F.A. & Tolstikov, G.A. Synthesis of (±)-recifeiolide. Chem Nat Compd 18, 267–270 (1982). https://doi.org/10.1007/BF00580448
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DOI: https://doi.org/10.1007/BF00580448