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Absolute configurations of brominated sesquiterpenes determined by vibrational circular dichroism.

Authors
  • Monde, Kenji
  • Taniguchi, Tohru
  • Miura, Nobuaki
  • Vairappan, Charles S
  • Suzuki, Minoru
Type
Published Article
Journal
Chirality
Publication Date
May 15, 2006
Volume
18
Issue
5
Pages
335–339
Identifiers
PMID: 16557523
Source
Medline
License
Unknown

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.

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