Structure assignment of aminoconduritols by 15N NMR correlation spectroscopy; synthesis of a positional isomer of 7-deoxypancratistatin

Stefan Schilling, Uwe Rinner, Collin Chan, Ion Ghiviriga, Tomas Hudlicky*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

20 Citations (Scopus)

Abstract

A positional isomer of 7-deoxypancratistatin was synthesized in 12 steps from epoxyaziridines 4 and 5. An intermolecular opening of the aziridine rather than the epoxide in the early stages of the synthesis led to 13, which did not match the properties of tetraacetate 10 derived from 7-deoxypancratistatin. At no stage of the synthesis did standard NMR techniques, involving 1H-1H or 1H-13C coupling, prove adequate for the structure assignment. Unambiguous structure was assigned by 1H-15N correlation NMR spectroscopy as well as by the conversion of epoxide 11 to diol 29 synthesized independently by another route. Experimental and spectral details are reported for all new compounds.

Original languageEnglish
Pages (from-to)1659-1667
Number of pages9
JournalCanadian Journal of Chemistry
Volume79
Issue number11
DOIs
Publication statusPublished - 2001

Keywords

  • N NMR spectroscopy
  • Aminoconduritols
  • Iso-7-deoxypancratistatin
  • Lewis acid catalyzed intramolecuar opening of epoxides

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

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