Absolute configurations of brominated sesquiterpenes determined by vibrational circular dichroism

Chirality. 2006 May 15;18(5):335-9. doi: 10.1002/chir.20259.

Abstract

Two brominated sesquiterpenes, majapolene B (1) and acetylmajapolene B (2), isolated from the red algal genus Laurencia were investigated using vibrational circular dichroism (VCD). The ab initio theoretical VCD and IR calculations of 1 and 2 were performed by density functional theory (DFT) using the B3PW91/6-31G(d,p) basis set. The experimental VCD spectra and corresponding population-weighted theoretical VCD spectra were found to be in excellent agreement in CCl(4) solution in the 1800-850 cm(-1) region, which allowed unambiguous determination of the absolute configurations of (-)-1 and (-)-2 as 7S,10S and 7S,10S, respectively.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bromine / chemistry*
  • Carbon Tetrachloride / chemistry
  • Circular Dichroism / methods*
  • Laurencia / chemistry
  • Methanol / chemistry
  • Models, Chemical
  • Molecular Structure
  • Plant Extracts / chemistry
  • Sesquiterpenes / analysis*
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification
  • Spectrophotometry, Infrared
  • Stereoisomerism

Substances

  • Plant Extracts
  • Sesquiterpenes
  • Carbon Tetrachloride
  • Bromine
  • Methanol