TY - JOUR
T1 - On the reactivity of 23-methoxycarbonyl furospirostanes
AU - MacÍas-Alonso, Mariana
AU - Flores-Álamo, Marcos
AU - Iglesias-Arteaga, Martin A.
N1 - Funding Information:
The authors thank to the Dirección General de Asuntos del Personal Académico (DGAPA-UNAM) for financial support via project IN221911-3 and CONACyT for scholarship granted to MM-A. Thanks are due to Nuria Esturau Escofet, Georgina Duarte Lisci and Victor Lemus Neri (USAI-UNAM) for recording NMR and MS spectra and Elemental Analysis. We are indebted to Dr. A. J. Boulton for his useful comments and for correcting the manuscript.
PY - 2011
Y1 - 2011
N2 - Brønsted and Lewis acid-catalysed reactions of the 23-methoxycarbonyl furospirostanic side chain are described. While bromination, deuteration and BF3·Et2O/AcOH treatment involve regioselective F-ring opening with exclusive participation of Δ22-furostenic intermediates, BF3·Et 2O/Ac2O treatment leads to irreversible E- or F-ring cleavage.
AB - Brønsted and Lewis acid-catalysed reactions of the 23-methoxycarbonyl furospirostanic side chain are described. While bromination, deuteration and BF3·Et2O/AcOH treatment involve regioselective F-ring opening with exclusive participation of Δ22-furostenic intermediates, BF3·Et 2O/Ac2O treatment leads to irreversible E- or F-ring cleavage.
KW - Bromination
KW - Brønsted acid-catalysed reactions
KW - Deuteration
KW - Furospirostanic side chain
KW - Lewis acid-catalysed reactions
KW - Rearrangements
UR - http://www.scopus.com/inward/record.url?scp=79960438324&partnerID=8YFLogxK
U2 - 10.1016/j.steroids.2011.04.006
DO - 10.1016/j.steroids.2011.04.006
M3 - Artículo
C2 - 21515298
SN - 0039-128X
VL - 76
SP - 1021
EP - 1031
JO - Steroids
JF - Steroids
IS - 10-11
ER -