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

作者:Giampa Geoffrey M; Fang Jian; Brewer Matthias*
来源:Organic Letters, 2016, 18(16): 3952-3955.
DOI:10.1021/acs.orglett.6b01674

摘要

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 the gives the desired tricyclic product as a single diastereomer. A gamma-amino-beta-hydroxy-alpha-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.

  • 出版日期2016-8-19