1990•Chemical and Pharmaceutical BulletinOpen access

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, S. FURUSAWA, Osamu Muraoka, T. ITOOKA

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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Key concepts: Bicyclic molecule, Aldol reaction, Chemistry, Decane, Intramolecular force, Stereochemistry, Intramolecular reaction, Bridged compounds