Expedient syntheses of antofine and cryptopleurine via intramolecular 1,3-dipolar cycloaddition.
The practical and expedient total syntheses of the representative phenanthroindolizidine and phenanthroquinolizidine alkaloids, antofine and cryptopleurine, are described. Construction of the pyrrolidine and piperidine ring of each alkaloid was achieved by using an intramolecular 1,3-dipolar cycloaddition of an azide onto an alkene and subsequent reduction of the resulting imine and aziridine.
Kim
Sanghee
S
College of Pharmacy, Seoul National University, San 56-1, Shilim, Kwanak, Seoul 151-742, Korea. pennkim@snu.ac.kr
Lee
Yun Mi
YM
Lee
Jaekwang
J
Lee
Taeho
T
Fu
Ye
Y
Song
Yanling
Y
Cho
Jihee
J
Kim
Deukjoon
D
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007536:Isomerism; D015394:Molecular Structure; D010618:Phenanthrolines / Q000138:chemical synthesis* / Q000737:chemistry
D000470:Alkaloids; D006571:Heterocyclic Compounds; D007211:Indoles; D010618:Phenanthrolines; C473343:antofine; C007160:cryptopleurine