ISSN : 0970 - 020X, ONLINE ISSN : 2231-5039
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Abstract

Design and Synthesis of New Dioxa-Diazaspiro[Bicyclo[9.4.2]Heptadecane-Steroid-Dienyne Derivative from Estrone and OTBS-Estrone

López-Ramos Maria1, Figueroa-Valverde Lauro1, Rosas-Nexticapa Marcela3, Herrera-Meza Maria Del Socorro4, Cervantes-Ortega Catalina3, Díaz-Cedillo Francisco2, García-Cervera Elodia1 and Pool-Gómez Eduardo1

DOI : http://dx.doi.org/10.13005/ojc/330301


Abstract:

Several bicycle-derivatives have been prepared using different protocols; nevertheless, expensive reagents and special conditions are required. The aim of this study was synthesize a dioxa-diazaspiro[bicyclo[9.4.2]heptadecane-steroid-dienyne derivative by a series of reactions which involving; a) alkinilization of estrone or OTBS-estrone with  5-hexyn-1-ol to form two propargyl alcohol derivatives (3 or 4); b) esterification 3 or 4 with succinic acid to form two dioxaspiro-steroid-cyclotridecan derivatives (5 or 6); c) preparation of diazaspiro[bicycle[9.4.2]heptadecane-steroid-4 amino complex (7 or 8) by reaction of 5 or 6 with ethylenediamine; d) removal of silyl fragment of 8 via hydrofluoric acid to form  the compound diazaspiro[bicycle[9.4.2]heptadecane-steroid-3´-ol (9); e) preparation of diazaspiro[bicycle[9.4.2]heptadecane-steroid-4-oxobutanoic acid (10) via esterification of 9 with succinic acid; f) amidation of 10 with ethylenediamine to form diazaspiro[bicyclo[9.4.2]heptadecane-steroid-4-aminobutanoate (11); g) synthesis of dioxadiazaspiro [bicyclo[9.4.2]heptadecane-steroid-dienyne (12) via pyrrolization of 11 using boric acid. The chemical structure of compounds was confirmed by NMR spectroscopic data.

Keywords:

OTB-estrone; Chemical synthesis

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