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Synlett 1996; 1996(12): 1173-1175
DOI: 10.1055/s-1996-5717
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Efficient Construction of Bi- and Tricyclic Cyclooctanoid Systems via Crossed [4+4]-Photocycloadditions of Pyran-2-ones1

Charles E. Chase, John A. Bender, F. G. West*
  • *Department of Chemistry, University of Utah, Salt Lake City, UT 84112
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Publication Date:
31 December 2000 (online)

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Pyran-2-ones connected to a pendant furan by a 3-carbon tether could be efficiently prepared in three steps. Irradiation in aqueous methanol furnished a mixture of endo and exo [4+4] adducts in good conversion when OR’ = carboxylate or sulfonate. In some cases, small amounts of cyclooctatriene resulting from decarboxylation of one or both diastereomers were isolated. Applicability of this approach to the tricyclic fusicoccane/ophiobolane skeleton was demonstrated by the conversion of 4i to 5i and 6i.

pyran-2-ones - furans - [4+4]-photocycloaddition - cyclooctadienes

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