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Synlett 1999; 1999(12): 1917-1918
DOI: 10.1055/s-1999-2980
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Novel Intramolecular Cyclisations Involving Ketene Radical Intermediates as an Approach to the Synthesis of Polyquinanes

Nicole M. Harrington-Frost* , Gerald Pattenden
  • *School of Chemistry, Nottingham University, Nottingham NG7 2RD, England; Fax + 44 115 9 51 35 35; E-mail: gp@nottingham.ac.uk
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Publication Date:
31 December 1999 (online)

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Treatment of the polyene selenyl ester 1 with Bu3SnH-AIBN leads to a concise synthesis of the diquinane 6 via a novel cyclisation involving a ketenyl radical intermediate. By contrast under the same radical initiating conditions the selenyl esters 2 and 10 produced cyclopentenone products, viz 9 and 11, and the allene substituted selenyl ester 16 led to the unusual cyclooctadienone 18.

cyclisations - tandem radical reactions