Diastereoselective manipulations of bicyclo[m.1.0]alkane derivatives. 3. Nucleophilic additions to the carbonyl carbon of (1R,8R)-bicyclo[6.1.0]nonan-2,6-dione2-(2S,3S)-1,4-di-O-methyl-1,2,3,4-butanetetrol ketal

Abstract

Abstract Conformations of the title compound were studied using a Monte Carlo search technique. Two principal conformational motifs were observed for the bicyclic carbocycle in which both faces of the carbonyl appear susceptible to nucleophilic attack. The title compound was synthesized in eight steps from cis-1,5-cyclooctanediol. Additions of nucleophiles (e.g., CH3Li) to the title compound gave adducts in good yields, but with low levels of diastereoselectivity, in agreement with computational prediction.