Synthesis of C-5′-alkyl substituted 17-spirofuran 19-norsteroids

Synthesis of C-5′-alkyl substituted 17-spirofuran 19-norsteroids

A number of new steroidal 17-spirofuran derivatives of the 19-nor series containing Me, Et or iPr-substituents in the heterocyclic moiety has been prepared, which are expected to have a strong progestagenic activity. The proposed approach made use of the 1-3-dipolar cycloaddition of low-molecular ni...

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Veröffentlicht in:Steroids 2001-07, Vol.66 (7), p.569-579
Hauptverfasser: Khripach, Vladimir A, Zhabinskii, Vladimir N, Tsavlovskii, Dmitrii N, Drachenova, Olga A, Ivanova, Galina V, Konstantinova, Olga V, Zavadskaya, Margarita I, Lyakhov, Alexander S, Govorova, Alla A, Groen, Marinus B, de Groot, Aede
Format: Artikel
Sprache:eng
Schlagworte:
1,3-Dipolar cycloaddition
19-Norsteroids
Acetylenic alcohols
Alicyclic compounds, terpenoids, prostaglandins, steroids
Animals
Chemistry
EPS
Exact sciences and technology
Furans - chemical synthesis
Humans
Laboratorium voor Organische chemie
Laboratory for Organic Chemistry
Nitrile oxides
Norsteroids - chemical synthesis
Organic Chemistry
Organische Chemie
Preparations and properties
Progesterone - analogs & derivatives
Spiro Compounds - chemical synthesis
Spirofurans
Steroids
Structure-Activity Relationship
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Beschreibung
Zusammenfassung:A number of new steroidal 17-spirofuran derivatives of the 19-nor series containing Me, Et or iPr-substituents in the heterocyclic moiety has been prepared, which are expected to have a strong progestagenic activity. The proposed approach made use of the 1-3-dipolar cycloaddition of low-molecular nitrile oxides with steroidal acetylenic alcohols followed by transformation of the isoxazole side chain.
ISSN:0039-128X
1878-5867
DOI:10.1016/S0039-128X(00)00222-1