TY - JOUR
T1 - Absolute Configuration Assignment of 3′,4′-di-O-acylkhellactones Using Vibrational Circular Dichroism Exciton Chirality
AU - Buendía-Trujillo, Abigail I.
AU - Torrres-Valencia, J. Martín
AU - Joseph-Nathan, Pedro
AU - Burgueño-Tapia, Eleuterio
N1 - Publisher Copyright:
© 2015 SAGE Publications Inc.
PY - 2015
Y1 - 2015
N2 - The 3′R,4‘R absolute configuration (AC) of the angular-type pyranocoumarins (-)-3′,4′-di-O-acetylkhellactone (2), (-)-4′-O-acetyl-3′-O-angeloylkhellactone (3), (+)-3′-O-acetyl-4-O-isobutyroylkhellactone (4), and (-)-3′-O-angeloyl-4′-O-senecioylkhellactone (5), isolated from the aerial parts of Prionosciadum thapsoides, was assigned by vibrational circular dichroism exciton chirality (VCDEC), and confirmed by comparison of their VCD frequencies with those calculated using DFT at the B3LYP/DGDZVP level. This again reveals that AC assignments based on optical rotation data are not very confident. Evaluation of Flack and Hooft parameters obtained after single-crystal X-ray diffraction analysis of 3, independently confirmed this AC.
AB - The 3′R,4‘R absolute configuration (AC) of the angular-type pyranocoumarins (-)-3′,4′-di-O-acetylkhellactone (2), (-)-4′-O-acetyl-3′-O-angeloylkhellactone (3), (+)-3′-O-acetyl-4-O-isobutyroylkhellactone (4), and (-)-3′-O-angeloyl-4′-O-senecioylkhellactone (5), isolated from the aerial parts of Prionosciadum thapsoides, was assigned by vibrational circular dichroism exciton chirality (VCDEC), and confirmed by comparison of their VCD frequencies with those calculated using DFT at the B3LYP/DGDZVP level. This again reveals that AC assignments based on optical rotation data are not very confident. Evaluation of Flack and Hooft parameters obtained after single-crystal X-ray diffraction analysis of 3, independently confirmed this AC.
KW - Absolute configuration
KW - Khellactone derivatives
KW - Prionosciadium thapsoides
KW - Vibrational circular dichroism exciton chirality
KW - X-Ray diffraction
UR - http://www.scopus.com/inward/record.url?scp=84969319566&partnerID=8YFLogxK
U2 - 10.1177/1934578X1501000658
DO - 10.1177/1934578X1501000658
M3 - Artículo
SN - 1934-578X
VL - 10
JO - Natural Product Communications
JF - Natural Product Communications
IS - 6
ER -