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Synlett 1993; 1993(6): 415-417
DOI: 10.1055/s-1993-22477
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Spiro[cyclopropane-1,4′-[2]oxabicyclo[3.2.0]hept-1(5)-en]-3′-one and its Δ1,7 Isomer from Diastereomeric Selenoxides

H. Martin R. Hoffmann* , Andreas Wulferding
  • *Department of Organic Chemistry, University of Hannover, Schneiderberg 1B, D-3000 Hannover, Germany
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Publication Date:
19 March 2002 (online)

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The title olefins are generated by selenoxide pyrolysis and trapped by Diels-Alder additions. Diastereomerically pure selenoxide is isolated and shown to equilibrate (6 : 1) with its epimer in the presence of water at room temperature. 5-Oxaspiro [2.4]-6-vinyl-6-hepten-4-one (9) is a new Diels-Alder diene for the simple construction of terpenoid lactones.