Synthesis of Two Novel Spiro Lactones Related to the B/C Ring System of Bakkenolides by Radical Cyclization

Thomas G. Back; Patricia L. Gladstone

doi:10.1055/s-1993-22577

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Synlett 1993; 1993(9): 699-700
DOI: 10.1055/s-1993-22577

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Synthesis of Two Novel Spiro Lactones Related to the B/C Ring System of Bakkenolides by Radical Cyclization

Thomas G. Back^* , Patricia L. Gladstone

^*Department of Chemistry, University of Calgary, Calgary, Alberta T2N 1N4, Canada

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Publication History

Publication Date:
19 March 2002 (online)

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The preparation of spiro lactones 2a and 2b was achieved by photochemically induced free-radical cyclization of allyl 1-(phenylseleno)-3-methyl-2-oxo-3-cyclopentenecarboxylate (4a) and its 4-methyl isomer (4b), respectively, followed by selenoxide elimination.