35162-65-3Relevant academic research and scientific papers
Reactions of Triterpenes: Part I - Oxidation of Friedelin with Hydrogen Peroxide in Presence of Selenium Dioxide
Anjaneyulu, V.,Rao, G. Sambasiva
, p. 663 - 664 (2007/10/02)
The oxidation of friedelin (6) with hydrogen peroxide in the presence of selenium dioxide in t-butanol gives friedel-1-en-3-one (8), friedelolactone (9), A-nor-friedelan-2-carboxylic acid and 2,3-seco-friedelane dicarboxylic acid.The last two compounds have been identified as the monoester (13) and the diester (7) respectively.
Terpenoids and Related Compounds: Part XXIII - Mechanism of Some Transformation Reactions of Friedelin and Its Derivatives
Talapatra, Bani,Lahiri, Biswanath,Basak, Amit,Pradhan, Dilip K.,Talapatra, Sunil K.
, p. 741 - 745 (2007/10/02)
DDQ dehydrogenation of friedelin (I) affords friedel-1-ene-3-one (III) in a very low yield (9percent).Treatment of 2α-bromofriedel-3-one (IV) with LiBr and Li2CO3 furnishes (III) (20percent) along with I (15percent).Reaction of IV with AgOAc and glacial HOAc leads to the formation of 3-hydroxyfriedel-3-ene-2-one (V) (66percent).Baeyer-Villiger oxidation of I with p-nitroperbenzoic acid produces the ε-lactone (IX) (41percent) while NiO2 oxidation of cerin (II) affords (V) (20percent) and 3α-hydroxyfriedel-2-one (VI) (15percent).The mechanism of these reactions are discussed.
