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Vibrational Circular Dichroism (VCD), VCD Exciton Coupling, and X‐ray Determination of the Absolute Configuration of an α , β ‐Unsaturated Germacranolide
Author(s) -
SánchezCastellanos Mariano,
Bucio María A.,
HernándezBarragán Angelina,
JosephNathan Pedro,
Cuevas Gabriel,
Quijano Leovigildo
Publication year - 2015
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.22420
Subject(s) - chemistry , vibrational circular dichroism , absolute configuration , circular dichroism , germacranolide , exciton , coupling (piping) , stereochemistry , lactone , physics , quantum mechanics , mechanical engineering , engineering
The absolute configuration of 1 was deduced by vibrational circular dichroism together with the evaluation of the Flack and Hooft X‐ray parameters. Vibrational circular dichroism exciton coupling, using the carbonyl group signals, confirmed the absolute configuration of 2 . In addition, sodium borohydride reduction of the 11,13‐double bond of 6‐ epi ‐desacetyllaurenobiolide ( 1 ) yields an almost equimolecular mixture of C11 epimers, while reduction of the same double bond of 6‐ epi ‐laurenobiolide ( 2 ) provided almost exclusively the (11 S ) diastereoisomer 4 . Chirality 27:247–252, 2015 . © 2015 Wiley Periodicals, Inc.