Synthesis of steroidal cyclopropanes

R. Ikan; A. Markus; Z. Goldschmidt

doi:10.1039/P19720002423

Synthesis of steroidal cyclopropanes

R. Ikan
, A. Markus
, Z. Goldschmidt

Department of Chemistry

Hebrew University of Jerusalem

Research output: Contribution to journal › Article › peer-review

14 Scopus citations

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.

Original language	English
Pages (from-to)	2423-2425
Number of pages	3
Journal	Journal of the Chemical Society, Perkin Transactions 1
DOIs	https://doi.org/10.1039/P19720002423
State	Published - 1972

Access to Document

10.1039/P19720002423

Cite this

@article{6d6a0bf0e2e647abb776d0ab2f34a08c,

title = "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.",

author = "R. Ikan and A. Markus and Z. Goldschmidt",

year = "1972",

doi = "10.1039/P19720002423",

language = "אנגלית",

pages = "2423--2425",

journal = "Journal of the Chemical Society, Perkin Transactions 1",

issn = "1472-7781",

publisher = "Chemical Society",

}

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 - https://www.scopus.com/pages/publications/0015451937

U2 - 10.1039/P19720002423

DO - 10.1039/P19720002423

M3 - ???researchoutput.researchoutputtypes.contributiontojournal.article???

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 -

Synthesis of steroidal cyclopropanes

Abstract

Access to Document

Other files and links

Fingerprint

Cite this