Conformational Analysis of (+)-Germacrene A by Variable Temperature NMR and NOE Spectroscopy.
(+)-Germacrene A, an important intermediate in sesquiterpene biosynthesis, was isolated in pure form from a genetically engineered yeast and was characterized by chromatographic properties (TLC, GC), MS, optical rotation, UV, IR, (1)H NMR and (13)C NMR data. Variable-temperature 500 MHz (1)H NMR spectra in CDCl(3) showed that this flexible cyclodecadiene ring exists as three NMR-distinguishable conformational isomers in a ratio of about 5:3:2 at or below ordinary probe temperature (25° C). The conformer structures were assigned by (1)H NMR data comparisons, NOE experiments, and vicinal couplings as follows: 1a (52%, UU), 1b (29% UD), and 1c (19%, DU).
Faraldos
Juan A
JA
Department of Chemistry, University of Illinois, 600 South Mathews Avenue, Urbana, IL 61801, USA.
Wu
Shuiqin
S
Chappell
Joe
J
Coates
Robert M
RM