Asymmetric synthesis of double bond isomers of the structure proposed for pyrinodemin A and indication of its structural revision

Molecules. 2005 Jan 31;10(1):312-6. doi: 10.3390/10010312.

Abstract

Asymmetric synthesis of double bond isomers (+)-2 (delta(15',16')) and (+)-3 (delta(14',15')) of the structure (1) (delta(16',17')) proposed for pyrinodemin A, a cytotoxic bis-pyridine alkaloid with a unique cis-cyclopent[c]isoxazolidine moiety from a marine sponge, has been accomplished. Pyrinodemin A was indicated to be a 1:1 racemic mixture of 2 from comparison of C(18 )and chiral HPLC analysis for pyrinodemin A and the synthetic compounds as well as ESIMS data of oxidative degradation products of pyrinodemin A.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chromatography, High Pressure Liquid
  • Isomerism
  • Models, Biological
  • Molecular Conformation
  • Oxazoles / chemical synthesis*
  • Oxazoles / chemistry*
  • Pyridines / chemical synthesis*
  • Pyridines / chemistry*

Substances

  • Oxazoles
  • Pyridines
  • pyrinodemin A