Structural revision of cephalosporolide J and bassianolone

J Org Chem. 2014 Feb 7;79(3):1493-7. doi: 10.1021/jo402602h. Epub 2014 Jan 22.

Abstract

The NMR spectra for three "natural" products: cephalosporolide C (Ces-C), cephalosporolide J (Ces-J), and bassianolone were found to be identical, and we proposed that Ces-C was the correct structure for the reported spectra. The first total synthesis of the proposed structure for Ces-J was achieved to support our structural revision for Ces-J. Chemical transformations of bassianolone and computational prediction of (13)C NMR spectra allowed us to conclude that Ces-C was the correct structure for bassianolone. Our synthetic and computational studies suggested that these "different" natural products Ces-C, Ces-J, and bassianolone have the same structure: Ces-C.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Butyrolactone / analogs & derivatives*
  • 4-Butyrolactone / chemical synthesis
  • 4-Butyrolactone / chemistry
  • Biological Products / chemistry
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry*
  • Stereoisomerism

Substances

  • Biological Products
  • Spiro Compounds
  • cephalosporolide C
  • cephalosporolide J
  • 4-Butyrolactone