Asymmetric synthesis of (R)-antofine and (R)-cryptopleurine via proline-catalyzed sequential α-aminoxylation and Horner-Wadsworth-Emmons olefination of aldehyde.
Naturally occurring phenanthroindolizidine alkaloids (R)-antofine and phenanthroquinolizidine alkaloids (R)-cryptopleurine have been synthesized in high optical purity via proline-catalyzed sequential α-aminoxylation and Horner-Wadsworth-Emmons olefination of aldehyde. Both enantiopure forms of proline are commercially available, and thus, in principle, both isomers of antofine and cryptopleurine can be accessed with the new method.
Cui
Mingbo
M
State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, People's Republic of China.
Song
Hongjian
H
Feng
Anzheng
A
Wang
Ziwen
Z
Wang
Qingmin
Q
D000447:Aldehydes / Q000737:chemistry*; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010618:Phenanthrolines / Q000138:chemical synthesis* / Q000737:chemistry; D011392:Proline / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D000470:Alkaloids; D007211:Indoles; D010618:Phenanthrolines; C473343:antofine; C007160:cryptopleurine; D011392:Proline