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Communication | Regular issue | Vol 12, No. 1, 1979, pp.37-39
Published online, 1st January, 1970
DOI: 10.3987/R-1979-01-0037
Bicyclo[3.3.1]nonanes as Synthetic Intermediates VI. An Oxaadamantanol Intermediate which Functions in the Highly Chemoselective Ring-enlargement of Bicyclo[3.3.1]nonane-3,7-dione by Diazomethane

Takefumi Momose,* Isamu Muraoka, and Shohgo Atarashi

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


The chemoselective synthesis of bicyclo[4.3.1]decane-3,8-dione (3) and 8-hydroxytricyclo [,8]decan-4-one (4) from bicyclo[3.3.1]nonane-3,7-dione (1) is described. Formation of an oxaadamantanol intermediate was shown to conduct the reaction and to realize its high chemoselectivity, because the monoketone bicyclo[3.3.1]nonan-3-one (5) failed to react with diazomethane.