TY - JOUR
T1 - Studies on the BF3·Et2O catalyzed Baeyer-Villiger reaction of spiroketalic steroidal ketones
AU - MacIas-Alonso, Mariana
AU - Morzycki, Jacek W.
AU - Iglesias-Arteaga, Martin A.
N1 - Funding Information:
The authors thank the Dirección General de Asuntos del Personal Académico (DGAPA-UNAM) for financial support via project IN204008-3 and CONACyT for scholarship granted to MM-A. Financial support from the University of Białystok within the project BST 124 is gratefully acknowledged. Thanks are due to Rosa I. del Villar Morales, Georgina Duarte Lisci (USAI-UNAM) for recording NMR and mass spectra.
PY - 2011/2
Y1 - 2011/2
N2 - During reactions of 23-oxosapogenins and the corresponding isomeric 22-oxo-23-spiroketals with MCPBA in the presence of BF3· Et2O, equilibration occurs between the ketones. The Baeyer-Villiger type oxidation is followed by fragmentation to the dinorcholanic lactones and 3-methylbutyrolactone. The mechanistic aspects of these reactions in the 25R and 25S series are discussed.
AB - During reactions of 23-oxosapogenins and the corresponding isomeric 22-oxo-23-spiroketals with MCPBA in the presence of BF3· Et2O, equilibration occurs between the ketones. The Baeyer-Villiger type oxidation is followed by fragmentation to the dinorcholanic lactones and 3-methylbutyrolactone. The mechanistic aspects of these reactions in the 25R and 25S series are discussed.
KW - 16β,23:23,26-Diepoxy-cholestan-22-ones
KW - 23-Oxosapogenins
KW - Baeyer-Villiger reaction
KW - Dinorcholanic lactones
UR - http://www.scopus.com/inward/record.url?scp=78751647660&partnerID=8YFLogxK
U2 - 10.1016/j.steroids.2010.12.004
DO - 10.1016/j.steroids.2010.12.004
M3 - Artículo
C2 - 21167855
SN - 0039-128X
VL - 76
SP - 317
EP - 323
JO - Steroids
JF - Steroids
IS - 3
ER -