TY - JOUR
T1 - Mechanistic insights on the reactivity of furospirostanes with the 16β,22:22,25-diepoxy-23-acetoxymethyl-24-methyl side chain
AU - Macias-Alonso, Mariana
AU - Flores-Alamo, 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 and CONACyT for scholarship granted to MM-A. Thanks are due to Rosa I. del Villar Morales, Georgina Duarte Lisci (USAI-UNAM) for recording NMR and MS spectra. We want to express our gratitude to Dr. Carlos Cobas from Mestrelab® for assistance with the MestreNova NMR processing program and to Dr. John Boulton for correcting the manuscript.
PY - 2013
Y1 - 2013
N2 - F-ring opening in spirostanes with the 16b,22:22,25-diepoxy-23- acetoxymethyl-24-methyl side chain produces a D22-intermediate with an allylic acetoxy group. For this reason the reactivity profile of these compounds deviates from that observed in other naturally occurring or synthetic spirostanes and furospirostanes.
AB - F-ring opening in spirostanes with the 16b,22:22,25-diepoxy-23- acetoxymethyl-24-methyl side chain produces a D22-intermediate with an allylic acetoxy group. For this reason the reactivity profile of these compounds deviates from that observed in other naturally occurring or synthetic spirostanes and furospirostanes.
KW - Allylic substitution
KW - Bromination
KW - Bromodeacetoxylation
KW - Elimination
KW - Furospirostanes
UR - http://www.scopus.com/inward/record.url?scp=84885016446&partnerID=8YFLogxK
U2 - 10.1016/j.steroids.2013.05.014
DO - 10.1016/j.steroids.2013.05.014
M3 - Artículo
C2 - 23707575
SN - 0039-128X
VL - 78
SP - 787
EP - 797
JO - Steroids
JF - Steroids
IS - 9
ER -