Cyclopentanoids constitute an exploding area of natural and non-natural producb. Several of these have proven to possess biological activities. Consequently, during the past decade, a large number of methods have been developed for cyclopentane annulations.' The construction of bi-and tricyclopentanoid skeletons has been in the forefront of research interest. The tricyclooctanones 2 can be readily produced in high yields from benzene and derivatives, via the triplet-sensitized oxa-di-a-methane rearrangement of bicyclo[2.2.2loctenone 1 as the photochemical key reaction.2 It was felt that photochemical rearrangement of an &y-unsaturated bicyclo[3.2.lloctenone 3 would produce the 1,3-acyl shift product, cis-fused enone 4, which would be a useful precursor of iridoids (Scheme I). We now report the preparation and photochemistry of enone 3. Formal synthesis of (A)-mussaenoside (5) and (*)-8-epiloganin (6) aglucones also are described.
Results and Discussion
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