Vibrational circular dichroism (VCD), VCD exciton coupling, and X-ray determination of the absolute configuration of an α,β-unsaturated germacranolide

Chirality. 2015 Mar;27(3):247-52. doi: 10.1002/chir.22420. Epub 2015 Jan 30.

Abstract

The absolute configuration of was deduced by vibrational circular dichroism together with the evaluation of the Flack and Hooft X-ray parameters. Vibrational circular dichroism exciton coupling, using the carbonyl group signals, confirmed the absolute configuration of . In addition, sodium borohydride reduction of the 11,13-double bond of 6-epi-desacetyllaurenobiolide () yields an almost equimolecular mixture of C11 epimers, while reduction of the same double bond of 6-epi-laurenobiolide () provided almost exclusively the (11S) diastereoisomer .

Keywords: 6-epi-desacetyllaurenobiolide; X-ray; diastereoselective reduction; exciton coupling; vibrational circular dichroism.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Circular Dichroism
  • Molecular Conformation
  • Sesquiterpenes, Germacrane / chemistry*
  • Vibration
  • X-Ray Diffraction

Substances

  • Sesquiterpenes, Germacrane
  • germacranolide