Collect. Czech. Chem. Commun. 1986, 51, 429-435

The synthesis of 5,6-cyclopropanocholestanes with oxygen functions in positions 3 and 7

Ladislav Kohout

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


The Simmons-Smith methylenation of the double bond in 3β-acetoxycholest-5-en-7-ols takes place selectively under formation of an adduct the configuration of which is determined by the configuration of the 7-hydroxyl group: 7β-alcohol IV gave 5β,6β-cyclopropane derivative VI, 7α-alcohol V gave 5α,6α-cyclopropane derivative VIII. On photochemically initiated cyclization of 3β-acetoxy-B-homo-5-en-7a-one (XIII) we obtained the product with an α-cyclopropane ring exclusively, i.e. 3β-acetoxy-5,6α-cyclopropano-5α-cholestan-7-one (XII).