Issue 0, 1972

Synthesis of steroidal cyclopropanes

Abstract

22,23-Methylenestigmast-5-en-3β-ol (IX), 24,25-methylenecholest-5-en-3β-ol (VII) and 24,25-methylene-lanost-8-en-3β-ol (XI) were synthesized by treating stigmasterol, desmosterol, and lanosterol with dichloro-carbene and reducing the adducts (VIII) and (VI) formed. Desmosteryl acetate (V) was synthesized by a novel method from 3β-acetoxychol-5-en-24-oic acid (I), the essential steps being preparation of the diazo-ketone (II), its photochemical Wolff rearrangement to the methyl ester (III), a Grignard reaction of (III) with methylmagnesium iodide and dehydration of the product.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1972, 2423-2425

Synthesis of steroidal cyclopropanes

R. Ikan, A. Markus and Z. Goldschmidt, J. Chem. Soc., Perkin Trans. 1, 1972, 2423 DOI: 10.1039/P19720002423

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