17947-03-4Relevant academic research and scientific papers
Friedelanes of Quercus suber Linn.: Behaviour of Cerin, Its Acetate and Other Related Triterpenoids towards Silica Gel and Alumina
Patra, Amarendra,Chaudhuri, Swapan Kumar
, p. 1152 - 1153 (2007/10/02)
A new pentacyclic triterpene, friedelan-3-one-2α-yl acetate (= cerin acetate) in addition to friedelin, cerin, 3-hydroxyfriedel-3-en-2-one. 3α-hydroxyfriedelan-2-one and canophyllol have been isolated from (Quercus suber Linn; fam Fagaceae).It is noted that cerin, its acetate and other closely related compounds undergo transformation in both silica gel and alumina (basic/neutral).
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.
