Absolute Configuration of the Ocimene Monoterpeniods from Artemisia absinthium
The absolute configuration (AC) of the naturally occurring ocimenes (−)‐(3S,5Z)‐2,6‐dimethyl‐2,3‐epoxyocta‐5,7‐diene (1) and (−)‐(3S,5Z)‐2,6‐dimethylocta‐5,7‐dien‐2,3‐diol (2), isolated from the essential oils of domesticated specimens of Artemisia absinthium, followed by vibrational circular dichroism (VCD) studies of 1, as well as from the acetonide 3 and the monoacetate 4, both derived from 2, since secondary alcohols are not the best functional groups to be present during VCD studies in solution due to intermolecular associations. The AC follows from comparison of experimental and calculated VCD spectra that were obtained by Density Functional Theory computation at the B3LYP/DGDZVP level of theory. Careful nuclear magnetic resonance (NMR) measurements were compared with literature values, providing for the first time systematic 1H and 13C chemical shift data. Regarding homonuclear 1H coupling constants, after performing a few irradiation experiments that showed the presence of several small long‐range interactions, the complete set of coupling constants for 3, which is representative of the four studied molecules, was determined by iterations using the PERCH software. This procedure even allowed assigning the pro‐R and pro‐S methyl group signals of the two gem‐dimethyl groups present in 3.
Main Authors: | Julio, Luis Fernando, Burgueño-Tapia, Eleuterio, Díaz, Carmen E., Pérez-Hernández, Nury, González-Coloma, Azucena, Joseph-Nathan, Pedro |
---|---|
Other Authors: | Ministerio de Economía y Competitividad (España) |
Format: | artículo biblioteca |
Language: | English |
Published: |
2017-08-25
|
Subjects: | ocimenes, Absolute configuration, |
Online Access: | http://hdl.handle.net/10261/204101 http://dx.doi.org/10.13039/501100003329 |
Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
Similar Items
-
Absolute configuration of the ocimene monoterpenoids from Artemisia absinthium
by: Julio, Luis F., et al.
Published: (2017-11) -
Absolute configuration of the ocimene monoterpenoids from Artemisia absinthium
by: Julio, Luis F., et al.
Published: (2017-11) -
Absolute configuration of indoline alkaloids from Geissospermum reticulatum
by: Gordillo-Román, Bárbara, et al.
Published: (2013-03-27) -
Alkyl Galactopyranosides: Rotational Population Dependence of the Hydroxymethyl Group on the Aglycon and Its Absolute Configuration and on the Anomeric Configuration
by: Padrón, Juan I., et al.
Published: (1998-10-29) -
Absolute configuration of tropane alkaloids from Schizanthus species by vibrational circular dichroism
by: Reina, Matías, et al.
Published: (2010-05)