Bicyclo[3.3.1]nonanes as Synthetic Intermediates. XVII. : A Novel Interconversion between Bicyclo-[4.3.1]decane and Tricyclo[4.3.1.0]decane Systems via the Dual Mode of Aldol Cyclization of Bicyclo-[4.3.1]decane-3, 8-dione

Takefumi MOMOSE; Kikuo MASUDA; Sachiko FURUSAWA; Osamu MURAOKA; Toshiyuki ITOOKA

doi:10.1248/cpb.38.1707

Takefumi MOMOSE, Kikuo MASUDA, Sachiko FURUSAWA, Osamu MURAOKA, Toshiyuki ITOOKA

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Keywords: ring expansion, bicyclo[3.3.1]nonane-3, 7-dione, aldol cyclization, bicyclo[4.3.1]decane-3, 8-dione, tricyclo[4.3.1.0]-decane, isotwistane, protoadamantane

JOURNAL FREE ACCESS

1990 Volume 38 Issue 6 Pages 1707-1711

DOI https://doi.org/10.1248/cpb.38.1707

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Abstract

The characteristics intramolecular aldol cyclization of bicyclo[4.3.1]decanedione to two novel tricyclic systems, protoadamantanone and isotwistanone, is described. Both systems were reconverted to bicyclo[4.3.1]decanones by the Grob fragmentation.

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