871926-94-2Relevant academic research and scientific papers
CAN-mediated oxidative cleavage of 4-aryl-3,4-dihydroxypiperidines
Chang, Meng-Yang,Lin, Chun-Yu,Pai, Chun-Li
, p. 2565 - 2568 (2007/10/03)
A CAN-mediated oxidative cleavage of 4-aryl-3,4-dihydroxypiperidines 2Aa-Be to β-amino carbonyl compounds 3Aa-Be and 4Aa-Be in different ratios is described. This facile strategy was also used to synthesize racemic fluoxetine (5).
Synthesis of (±)-coerulescine and a formal synthesis of (±)-horsfiline
Chang, Meng-Yang,Pai, Chun-Li,Kung, Yung-Hua
, p. 8463 - 8465 (2007/10/03)
A straightforward synthesis of (±)-coerulescine and (±)-horsfiline has been established from 3-formyl-3-phenylpyrrolidine employing 4-hydroxypiperidine as the starting material. There are two remarkable steps for the synthesis of (±)-coerulescine and (±)-horsfiline. One is the rapid access to produce 3-formyl-3-phenylpyrrolidine by Lewis acid-catalyzed rearrangement of 3,4-dihydroxy-4-phenylpiperidine. The other key step is an intramolecular electrophilic cyclization from 3-benzylcarbamoyl-3- phenylpyrrolidine to the 3,3-spirocyclic 2-oxindole ring skeleton.
