First enantiospecific total synthesis of the important biogenetic intermediates, (+)-polyneuridine and (+)-polyneuridine aldehyde, as well as 16-epi-vellosimine and macusine A

Org Lett. 2007 Jan 18;9(2):295-8. doi: 10.1021/ol062762q.

Abstract

The first enantiospecific total synthesis of the alkaloids 16-epi-vellosimine (1), (+)-polyneuridine (2), (+)-polyneuridine aldehyde (3), and macusine A (4) is reported. The key oxidation was accomplished with the Corey-Kim reagent to provide the important biogenetic intermediates, 16-epi-vellosimine (1) and polyneuridine aldehyde (3), the latter of which is required for the conversion of the sarpagan skeleton into the ajmalan system in the biosynthesis of quebrachidine. [reaction: see text].

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Aldehydes / chemical synthesis*
  • Aldehydes / chemistry
  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry
  • Indole Alkaloids / chemical synthesis*
  • Indole Alkaloids / chemistry
  • Molecular Structure
  • Oxidation-Reduction
  • Stereoisomerism

Substances

  • 16-epi-vellosimine
  • Aldehydes
  • Alkaloids
  • Indole Alkaloids
  • polyneuridine
  • polyneuridine aldehyde
  • macusine A