Concise route to triquinanes from pyran-2-ones.
Treatment of ether-bridged cyclooctatrienes (formed via intramolecular [4 + 4]-photocycloaddition of pyran-2-ones bearing pendent furans, followed by thermal decarboxylation) with excess MeLi furnishes triquinane ring systems via an apparent sequence of beta-elimination, 1,5-hydrogen shift, and transannular aldolization.
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Department of Chemistry, University of Alberta, E3-43 Gunning-Lemieux Chemistry Centre, Edmonton, AB, T6G 2G2 Canada.
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Robert
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West
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