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Absolute stereochemistry of guaianolides, of matricin and its epimers, of yarrow proazulenes, and of chamazulene carboxylic acid
Author(s) -
Imming Peter,
Goeters Susanne,
Pawlitzki Gregor,
Hempel Bernd
Publication year - 2001
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.1041
Subject(s) - chemistry , epimer , absolute configuration , stereochemistry , absolute (philosophy) , carboxylic acid , chemical shift , organic chemistry , philosophy , epistemology
Known determinations of the absolute configuration of guaianolides were collected and found to be few. The absolute configurations of guaianolides rest on the assumption that 7‐H always has α‐orientation. For matricin, only the relative configuration was determined. On the basis of a detailed study of the NMR spectra of matricin and its epimers, and of synthetic, NMR, and CD studies with its decomposition product, chamazulene carboxylic acid, we were able to reconfirm the accepted 3S,3aR,4S,9R,9aS,9bS configuration of matricin. Chirality 13:337–341, 2001. © 2001 Wiley‐Liss, Inc.