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Absolute configurations of brominated sesquiterpenes determined by vibrational circular dichroism

✍ Scribed by Kenji Monde; Tohru Taniguchi; Nobuaki Miura; Charles S. Vairappan; Minoru Suzuki

Publisher: John Wiley and Sons
Year: 2006
Tongue: English
Weight: 149 KB
Volume: 18
Category: Article
ISSN: 0899-0042
DOI: 10.1002/chir.20259

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✦ Synopsis

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 7__S__,10__S__ and 7__S__,10__S__, respectively. Chirality, 2006. © 2006 Wiley‐Liss, Inc.

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