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New approach to the aromatization of ring B in 19-norsteroids and to the synthesis of equilenin-type compounds

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1978
Authors
Mihailović, Mihailo Lj.
Foršek, J.
Lorenc, Ljubinka
Article (Published version)
,
Royal Society of Chemistry
Metadata
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Abstract
When 7α-acetoxy-3,3 : 17,17-bis(ethylenedioxy)-5,10-epoxy-5β, 10β-oestran-6-one (2), formed by lead tetra-acetate acetoxylation of the parent compound (1), is heated with alkali, it undergoes ring B aromatization to give 3,3: 17,17-bis(ethylenedioxy)-5(10),6,8-oestratriene-6,7-diol (3), without configurational change at C(14); deacetalization of the corresponding diacetate (4), followed by lead tetra-acetate aromatization of ring A in the resulting diketone (5), produces 6,7-diacetoxy-equilenin (6), which is finally converted into its 3-acetate (7).
Source:
Journal of the Chemical Society, Chemical Communications, 1978, 21, 916-918
Publisher:
  • Royal Society of Chemistry
Projects:
  • Serbian Republic Research Fund

DOI: 10.1039/C39780000916

ISSN: 0022-4936

Scopus: 2-s2.0-37049095357
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URI
http://cer.ihtm.bg.ac.rs/handle/123456789/2761
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IHTM

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