Total Syntheses with Tricyclooctanone Building Blocks. Synthesis of Iridodial

Article abstract of DOI:10.1021/jo00181a001

A total synthesis of the monoterpene iridodial, in 12 steps and 13percent overall yield from 1,3-cyclohexadiene, is described.The known (-)-tricyclo<3.3.0.0^2,8>octan-3-one, which is readily available in multigram batches and in high enantiomeric purity, served as the key intermediate.The subsequent transformations involved standard procedures, and seperations were only necessary in the two final steps.