Synthesis of steroidal cyclopropanes

R. Ikan, A. Markus, Z. Goldschmidt

Research output: Contribution to journalArticlepeer-review

14 Scopus citations


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.

Original languageEnglish
Pages (from-to)2423-2425
Number of pages3
JournalJournal of the Chemical Society, Perkin Transactions 1
StatePublished - 1972


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