Absolute configuration of esquelane derivatives from Adesmia boronioides by vibrational circular dichroism

[Display omitted] The absolute configurations of natural esquelane derivatives 1 and 2, the main components of a commercially available fragrance, as well as their synthetic derivatives 3–7 were revised by using the vibrational circular dichroism (VCD) spectroscopy of 2 and 6 in combination with den...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron: asymmetry Vol. 26; no. 2-3; pp. 136 - 140
Main Authors Cerda-García-Rojas, Carlos M., Bucio, María A., González, Silvia B., García-Gutiérrez, Hugo A., Joseph-Nathan, Pedro
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 15.02.2015
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
CACALOL
ESSENTIAL OIL
Online AccessGet full text

Cover

More Information
Summary:[Display omitted] The absolute configurations of natural esquelane derivatives 1 and 2, the main components of a commercially available fragrance, as well as their synthetic derivatives 3–7 were revised by using the vibrational circular dichroism (VCD) spectroscopy of 2 and 6 in combination with density functional theory calculations at the B3LYP/DGDZVP level of theory. The agreement between the experimental and calculated VCD spectra of these bisnorsesquiterpenes revealed that they are in fact (1S,4R,5S)-esquel-6-en-9-one 1 and (1S,4R,5R)-esquel-7-en-9-one 2 instead of the formerly reported enantiomers. The VCD method was also applied to cacalol acetate 9 in order to verify its absolute configuration, since cacalol 8 was previously used as a comparative motif to determine the absolute configuration of esquelane derivatives.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2014.12.003