[2.2.1]-Bicyclic systems relevant to synthetic studies on CP-225,917—use of a new silylated cyclopentadiene

The [2.2.1]-bicyclic ketone , a potential synthetic precursor to CP-225,917, was prepared by a sequence beginning with Diels–Alder reaction between dimethyl fumarate and the silylated cyclopentadiene . The adduct was subjected to Tamao–Fleming oxidation, which converted it into alcohol . During the oxidation BF3·Et2O–AcOH was used instead of the more expensive BF3·2AcOH complex. Alcohol was elaborated into , which carries one of the sidechains of CP-225,917, as well as other substituents that are appropriate for further elaboration.