A Route to the C,D,E Ring System of the Aspidosperma Alkaloids.

ABSTRACT: A short synthetic sequence leading to the formation of the C,D,E-ring subunit of the Aspidosperma alkaloids is reported. This route is based on a ring fragmentation/intramolecular azomethine ylide 1,3-dipolar cycloaddition reaction sequence that gives the desired tricyclic product as a single diastereomer. A γ-amino-β-hydroxy-α-diazo carbonyl compound is shown to fragment in the presence of a Lewis acid to give an iminium product that can be directly reduced to the corresponding amine.

SUBMITTER: Giampa GM 

PROVIDER: S-EPMC4994716 | biostudies-literature | 2016 Aug

REPOSITORIES: biostudies-literature