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Synlett 1995; 1995(8): 831-832
DOI: 10.1055/s-1995-5100
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Synthesis of Bicyclo[3.3.1]nonanes via Manganese(III) Mediated Radical Cyclization of Olefinic β-Keto Esters

James D. White* , Scott C. Jeffrey
  • *Department of Chemistry, Oregon State University, Corvallis, OR 97331-4003, USA
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Publication Date:
31 December 2000 (online)

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Oxidative cyclization of olefinic β-keto esters 11 and 19 with Mn(OAc)3.2H2O and Cu(OAc)2⋅H2O gave 12 and 23, respectively. These products are formed by initial cyclization to a bicyclo[3.3.1]nonane radical which abstracts a hydrogen atom from the N-ethyl substituent of a proximal amide. In the case of 19, a further cyclization of the resultant radical leads to 22 which is oxidized to 23.

huperzine - hydrogen atom transfer - N-deethylation