TY - JOUR
T1 - Design and synthesis of new dioxa diazaspiro[bicyclo [9.4.2] heptadecane-steroid-dienyne derivative from estrone and OTBS-estrone
AU - López-Ramos, Maria
AU - Figueroa-Valverde, Lauro
AU - Rosas-Nexticapa, Marcela
AU - Herrera-Meza, Maria Del Socorro
AU - Cervantes-Ortega, Catalina
AU - Díaz-Cedillo, Francisco
AU - García-Cervera, Elodia
AU - Pool-Gómez, Eduardo
N1 - Publisher Copyright:
© 2017, Oriental Scientific Publishing Company. All rights reserved.
PY - 2017
Y1 - 2017
N2 - 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.
AB - 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.
KW - Chemical synthesis
KW - OTB-estrone
UR - http://www.scopus.com/inward/record.url?scp=85025818034&partnerID=8YFLogxK
U2 - 10.13005/ojc/330301
DO - 10.13005/ojc/330301
M3 - Artículo
SN - 0970-020X
VL - 33
SP - 1061
EP - 1070
JO - Oriental Journal of Chemistry
JF - Oriental Journal of Chemistry
IS - 3
ER -