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Communication | Regular issue | Vol 12, No. 1, 1979, pp.41-44
Published online, 1st January, 1970
DOI: 10.3987/R-1979-01-0041
Site-specificity in the Baeyer-Villiger Oxidation of 2-Alkyl-9-azabicyclo[3.3.1]nonane-3,7-diones: Exclusive Cleavage of the Alkylated Half of the Twin-piperidinone System

Takefumi Momose,* Shohgo Atarashi, and Conrad Hans Eugster

*Faculty of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Toyonaka, Osaka 560-0043, Japan


The Baeyer-Villiger oxidation of 2-alkyl-N-methoxycarbonyl-9-azabicyclo[3.3.1]nonane-3,7-diones (9a and 9b) proceeded site-specifically to afford the keto lactones (11a and 11b) which were transformed into the cis-2.6-disubstituted piperidines related to palustramic acid.