871926-96-4Relevant academic research and scientific papers
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.
