title: General approach for the synthesis of sarpagine/ajmaline indole alkaloids. Stereospecific total synthesis of the sarpagine alkaloid (+)-vellosimine.
abstract: [reaction: see text] (+)-Vellosimine has been synthesized enantiospecifically in 27% overall yield from commercially available D-(+)-tryptophan methyl ester via the asymmetric Pictet-Spengler reaction and a stereocontrolled intramolecular palladium-coupling reaction as key steps.
authors.affiliation: Department of Chemistry, University of Wisconsin-Milwaukee, Milwaukee, Wisconsin 53211, USA.
authors.forename: T
authors.initials: T
authors.lastname: Wang
authors.forename: J M
authors.initials: JM
authors.lastname: Cook
mesh_terms: D000404:Ajmaline / Q000138:chemical synthesis*; D000447:Aldehydes / Q000737:chemistry; D000470:Alkaloids / Q000138:chemical synthesis*; D001938:Brazil; D002384:Catalysis; D007202:Indicators and Reagents; D007211:Indoles / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D010946:Plants, Medicinal / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000470:Alkaloids; D007202:Indicators and Reagents; D007211:Indoles; C413127:vellosimine; D000404:Ajmaline