TY - JOUR
T1 - Synthesis of steroidal cyclopropanes
AU - Ikan, R.
AU - Markus, A.
AU - Goldschmidt, Z.
PY - 1972
Y1 - 1972
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0015451937&partnerID=8YFLogxK
U2 - 10.1039/P19720002423
DO - 10.1039/P19720002423
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C2 - 4674538
AN - SCOPUS:0015451937
SN - 1472-7781
SP - 2423
EP - 2425
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
ER -