An efficient synthesis of 3-methoxy-19-norpregna-1,3,5(10),16-tetraen-20-one

An efficient preparative method for the synthesis of 3-methoxy-19-norpregna-1,3,5(10), 16-tetraen-20-one was suggested. This compound is a key intermediate product in the preparation of 3,20-dihydroxy-19-norpregnatrienes, antagonists of estrogen receptor and cytotoxic agents. The reaction of 16-dehy...

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Published in:Russian chemical bulletin 2018-11, Vol.67 (11), p.2112-2120
Main Authors: Kuznetsov, Yu. V., Levina, I. S., Shashkov, A. S., Zavarzin, I. V.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Dimers
Full Articles
Halides
Inorganic Chemistry
Magnesium
Organic Chemistry
Synthesis
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description An efficient preparative method for the synthesis of 3-methoxy-19-norpregna-1,3,5(10), 16-tetraen-20-one was suggested. This compound is a key intermediate product in the preparation of 3,20-dihydroxy-19-norpregnatrienes, antagonists of estrogen receptor and cytotoxic agents. The reaction of 16-dehydro-17-carbonitrile (obtained in two steps from estrone methyl ether) with methyl magnesium halides gave the target product in high yield. While studying this reaction, we isolated and characterized an unusual steroid dimer, a fused 16,17-pyridinosteroid substituted in the hetero ring of the second steroid molecule. A mechanism of its formation was suggested.
doi_str_mv 10.1007/s11172-018-2337-7
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subjects Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Dimers
Full Articles
Halides
Inorganic Chemistry
Magnesium
Organic Chemistry
Synthesis
title An efficient synthesis of 3-methoxy-19-norpregna-1,3,5(10),16-tetraen-20-one
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