35319-92-7Relevant academic research and scientific papers
Studies on the BF3·Et2O catalyzed Baeyer-Villiger reaction of spiroketalic steroidal ketones
MacIas-Alonso, Mariana,Morzycki, Jacek W.,Iglesias-Arteaga, Martin A.
, p. 317 - 323 (2011)
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.
On reactions of spirostane sapogenins with benzeneseleninic anhydride
Jastrzbska, Izabella,Dobrogowska, Aneta,Lutostańska, Ewa,Morzycki, Jacek W.
experimental part, p. 5024 - 5029 (2010/08/20)
Direct dehydrogenation of spirostane sapogenins with benzeneseleninic anhydride/iodoxybenzene afforded the Δ22 derivatives in low yields. The reactions catalyzed by BF3/Et2O produced the 23-oxo-sapogenins in addition to th
New bisfuran derivative from sarsasapogenin: An X-ray and NMR analysis
Lopez, Yliana,Santillan, Rosa,Farfan, Norberto
, p. 12 - 17 (2007/10/03)
The new bisfuran derivative, (22S,23S)-22,23-dihydroxy-23,26-epoxyfurostane (5), was obtained from the known oxidation of sarsasapogenin acetate with NaNO2/BF3 in 5% aqueous acetic acid. The structure of 5 was established using one and two-dimensional 1H, 13C experiments (DEPT, COSY, HETCOR and HMBC) and the configurations at the newly formed stereogenic centers were established as 22S,23S by an X-ray diffraction analysis. Addition of TiCl4 to bisfuran 5 confirmed that this compound is an intermediate in the rearrangement to 22-oxo-23-spiroketals since it was transformed quantitatively into the latter product. The 23-nitroimino intermediate 2 was isolated from the same reaction and its structure established also by an X-ray diffraction analysis; this compound was further transformed into the 23-nitramine 7 which could find application in functionalization of position 24.
