2466-25-3Relevant academic research and scientific papers
Expedited Baeyer-Villiger oxidation of steroidal ketones by microwave irradiation
Borah, Juri Moni,Chowdhury, Pritish
experimental part, p. 1341 - 1345 (2011/11/06)
Microwave (MW) assisted reactions are currently having considerable importance in the synthesis of organic compounds. Considering the remarkable application of Baeyer-Villiger (BV) reaction in the synthesis of natural products and steroid-peptide conjugates, we report here some of our findings of BV oxidation of carbonyl compounds with special reference to steroidal ketones under MW irradiation justifying its accelerating effect.
Ceric ammonium nitrate (CAN) catalyzed Baeyer-Villiger oxidation of carbonyl compounds, specially 20-oxosteroids
Goswami, Papori,Hazarika, Saroj,Das, Archana M.,Chowdhury, Pritish
, p. 1275 - 1281 (2007/10/03)
The role of ceric ammonium nitrate (CAN) as an effective catalyst in the peracid induced Baeyer-Villiger oxidation of carbonyl compounds with special reference to steroids has been demonstrated.
Photoinduced Transformations. 77. A Four-Step Substitution of a Carbonyl Group of Steroidal Ketones by an Oxygen Atom. A New Method for the Synthesis of Cyclic Ethers
Suginome, Hiroshi,Yamada, Shinji
, p. 2489 - 2494 (2007/10/02)
We set out to describe a new and versatile method for transforming steroidal five- and six-memered cyclic ketones as a starting materials into steroidal cyclic ethers with the same ring size via four steps; Baeyer-Villiger oxidation of steroidal ketone to a lactone followed by its reduction with DIBAL gives the corresponding lactol.The irradiation of the hypoiodite generated in situ by means of the reaction of the lactol by an excess of mercury(II)oxide-iodine and pyridine in benzene gives formates arising from a regiospecific β-scission of th C-C bond.These formates can read ily be transformed into oxasteroids by treatment with a complex metal hydride or methyllithium.By this new method a variety of steroidal cyclic ketones were transformed into the corresponding cyclic ethers in a good overall yields.The stereochemical integrity of the chiral center adjacent to the carbonyl group of the starting cyclic ketones is maintained throughout this transformation.
REPLACEMENT OF A CARBONYL GROUP OF CYCLIC KETONES BY AN OXYGEN ATOM: A FOUR-STEP TRANSFORMATION OF CYCLIC KETONES INTO CYCLIC ETHERS
Suginome, Hiroshi,Yamada, Shinji
, p. 3995 - 3998 (2007/10/02)
We describe a new and versatile method for transforming cyclic ketones into cyclic ethers with the same ring size in which the chirality adjacent to the carbonyl group of the ketones is retained.
