General approach for the synthesis of sarpagine/ajmaline indole alkaloids. Stereospecific total synthesis of the sarpagine alkaloid (+)-vellosimine.
[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.
Wang
T
T
Department of Chemistry, University of Wisconsin-Milwaukee, Milwaukee, Wisconsin 53211, USA.
Cook
J M
JM
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
D000447:Aldehydes; D000470:Alkaloids; D007202:Indicators and Reagents; D007211:Indoles; C413127:vellosimine; D000404:Ajmaline