(+)-Desoxoprosopinine: A Model for the Total Asymmetric Synthesis of Prosopis Alkaloids

Abstract

This work develops a general synthesis of the Prosopis africana alkaloids, using a chiral auxiliary-mediated process. Enantiopure N-acyldihydropyridones were produced and used as intermediates, targeting (+)-desoxoprosopinine as a synthetic model for those alkaloids. The orientation of all three stereocenters was highly controlled, with the synthesis of intermediate 75, just short of the target, in 7 steps with a 13.8% overall yield.

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Document Details

Document Type
Technical Report
Publication Date
Jan 01, 1999
Accession Number
ADA366524

Entities

People

  • Matthew J. Sandelier

Organizations

  • North Carolina State University

Tags

Communities of Interest

  • Biomedical

DTIC Thesaurus Topics

  • Air Force
  • Alcohols
  • Chemical Synthesis
  • Chemistry
  • Chlorides
  • Liquid Chromatography
  • Materials
  • Organic Chemistry
  • Organic Compounds
  • Spectra
  • Spectroscopy

Fields of Study

  • Chemistry

Readers

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  • Organic Chemistry