title: Asymmetric synthesis of (R)-antofine and (R)-cryptopleurine via proline-catalyzed sequential α-aminoxylation and Horner-Wadsworth-Emmons olefination of aldehyde.
abstract: 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.
authors.affiliation: State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, People's Republic of China.
authors.forename: Mingbo
authors.initials: M
authors.lastname: Cui
authors.forename: Hongjian
authors.initials: H
authors.lastname: Song
authors.forename: Anzheng
authors.initials: A
authors.lastname: Feng
authors.forename: Ziwen
authors.initials: Z
authors.lastname: Wang
authors.forename: Qingmin
authors.initials: Q
authors.lastname: Wang
mesh_terms: 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
chemical_list: D000447:Aldehydes; D000470:Alkaloids; D007211:Indoles; D010618:Phenanthrolines; C473343:antofine; C007160:cryptopleurine; D011392:Proline