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Determination of the absolute configuration of the natural product klaivanolide via density functional calculations of vibrational circular dichroism (VCD)
Author(s) -
Devlin Frank J.,
Stephens Philip J.,
Figadère Bruno
Publication year - 2009
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20776
Subject(s) - chemistry , vibrational circular dichroism , absolute configuration , circular dichroism , density functional theory , computational chemistry , stereochemistry
The absolute configuration (AC) of the antiprotozoal lactone, Klaivanolide, 1 , from Uvaria klaineana , has been determined using Vibrational Circular Dichroism (VCD) spectroscopy. The experimental VCD spectrum of the (+) enantiomer of 1 was measured. To analyze the AC of (+)‐ 1 , the conformationally‐averaged VCD spectrum of 7‐ S ‐ 1 was calculated using density functional theory (DFT) and the GAUSSIAN 03 program. The B3PW91/TZ2P conformationally‐averaged VCD spectrum of 7‐ S ‐ 1 proves that the AC of 1 is 7‐ S ‐(+). Chirality 21:E48–E53, 2009. © 2009 Wiley‐Liss, Inc.