Synthesis of vinca alkaloids and related compounds. 100. Stereoselective oxidation reactions of compounds with the aspidospermane and quebrachamine ring system. First synthesis of some alkaloids containing the epoxy ring.
The first syntheses of the alkaloids (-)-mehranine (3), (+)-voaphylline/conoflorine (4), (+)-N(a)-methylvoaphylline/hecubine (5), and (-)-lochnericine (2) were achieved by stereoselective epoxidation starting from (-)-tabersonine (1), through intermediates with the aspidospermane and quebrachamine skeleton.
Eles
János
J
Department for Organic Chemistry, Budapest University of Technology and Economics, Gellért tér 4, H-1111, Budapest, Hungary.
Kalaus
György
G
Greiner
István
I
Kajtár-Peredy
Mária
M
Szabó
Pál
P
Keserû
György Miklós
GM
Szabó
Lajos
L
Szántay
Csaba
C
D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D007202:Indicators and Reagents; D026121:Indole Alkaloids; D007211:Indoles / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D011804:Quinolines; D013237:Stereoisomerism; D014748:Vinca Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry
D000470:Alkaloids; D004852:Epoxy Compounds; D007202:Indicators and Reagents; D026121:Indole Alkaloids; D007211:Indoles; D011804:Quinolines; D014748:Vinca Alkaloids; C091897:quebrachamine; C091896:aspidospermine