Determination of the absolute stereochemistry of limonene and alpha-santalol by Raman optical activity spectroscopy

Nat Prod Commun. 2012 Apr;7(4):419-21.

Abstract

Determining the absolute stereochemistry of organic compounds in solution remains a challenge. We investigated the use of Raman optical activity (ROA) spectroscopy to address this problem. The absolute configurations of (+)-(R)- and (-)-(S)-limonene were determined by ROA spectroscopy, which can be applied to smaller amounts of sample as compared with vibrational circular dichroism (VCD) spectroscopy. This ROA method was also applied to (+)-(E)-alpha-santalol and shown to be successful in the determination of the absolute configuration of this compound. ROA spectroscopy shows promise as a useful tool for determining the absolute stereochemistry of many natural compounds.

MeSH terms

  • Cyclohexenes / chemistry*
  • Limonene
  • Polycyclic Sesquiterpenes
  • Sesquiterpenes / chemistry*
  • Spectrum Analysis, Raman
  • Stereoisomerism
  • Terpenes / chemistry*

Substances

  • Cyclohexenes
  • Polycyclic Sesquiterpenes
  • Sesquiterpenes
  • Terpenes
  • santalol
  • Limonene