title: A new approach for asymmetric synthesis of (R)-3-methylpyrrolidine alkaloids from (S)-malic acid.
abstract: Diastereoselective methylation of dimethyl (S)-malate 7, followed by two, three-step reductive de-hydroxylation procedures afforded dimethyl (R)-2-methylsuccinate 11 in 80.2% e.e. and 84.7% e.e., respectively. The latter compound was further transformed into the natural enantiomers of the ant venom alkaloids (R)-leptothoracine 1 and (R)-3-methyl-N-(2-phenylethyl)-pyrrolidine 2.
authors.affiliation: Department of Chemistry, Xiamen University, PR China.
authors.forename: Xiao
authors.initials: X
authors.lastname: Zheng
authors.forename: Pei-Qiang
authors.initials: PQ
authors.lastname: Huang
authors.forename: Yuan-Ping
authors.initials: YP
authors.lastname: Ruan
authors.forename: Albert W M
authors.initials: AW
authors.lastname: Lee
authors.forename: Wing Hong
authors.initials: WH
authors.lastname: Chan
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D002851:Chromatography, High Pressure Liquid; D008293:Malates / Q000737:chemistry*; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D008293:Malates; D011759:Pyrrolidines; C030298:malic acid