Toward general access to the aspidosperma-type terpenoid indole alkaloids: synthesis of the key 3,3-disubstituted piperidones through enantioselective intramolecular heck-type reaction of chloroformamides.
An enantioselective intramolecular Heck-type reaction of chloroformamides has been developed for the synthesis of 3,3-disubstituted piperidones. The desired piperidone was formed in the presence of a palladium catalyst, an optically active phosphoramidite ligand, K3PO4 and Ag3PO4. The obtained piperidone was converted to epieburnamonine.
Yasui
Yoshizumi
Y
Graduate School of Pharmaceutical Sciences, Kyoto University, Kyoto, Japan.
Takeda
Hiroshi
H
Takemoto
Yoshiji
Y
D000470:Alkaloids / Q000138:chemical synthesis*; D030009:Aspidosperma / Q000737:chemistry*; D002384:Catalysis; D002855:Chromatography, Thin Layer; D005559:Formamides / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D007211:Indoles / Q000138:chemical synthesis*; D010165:Palladium; D010710:Phosphates / Q000737:chemistry; D010881:Piperidones / Q000138:chemical synthesis* / Q000737:chemistry; D017680:Potassium Compounds / Q000737:chemistry; D018030:Silver Compounds / Q000737:chemistry; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis*
D000470:Alkaloids; D005559:Formamides; D007202:Indicators and Reagents; D007211:Indoles; D010710:Phosphates; D010881:Piperidones; D017680:Potassium Compounds; D018030:Silver Compounds; D013729:Terpenes; D010165:Palladium; C013216:potassium phosphate; C039072:silver phosphate