Artarborol, a nor-caryophyllane sesquiterpene alcohol from Artemisia arborescens. stereostructure assignment through concurrence of NMR data and computational analysis.
A nor-caryophyllane derivative, artarborol, has been isolated from wormwood (Artemisia arborescens) and its stereostructure established by using a combination of chemical derivatization, NMR data, molecular modeling, and quantum-mechanical calculations. In particular, comparison of experimental 13C NMR data with a Boltzmann-weighed average of 13C NMR chemical shifts, calculated by ab initio DFT method, supported the stereochemical assignment.
Fattorusso
Caterina
C
Dipartimento di Chimica delle Sostanze Naturali, Università di Napoli Federico II, Via D. Montesano 49, I-80131 Napoli, Italy.
Stendardo
Emiliano
E
Appendino
Giovanni
G
Fattorusso
Ernesto
E
Luciano
Paolo
P
Romano
Adriana
A
Taglialatela-Scafati
Orazio
O
D000438:Alcohols / Q000737:chemistry* / Q000302:isolation & purification; D019306:Artemisia / Q000737:chemistry*; D003198:Computer Simulation; D009682:Magnetic Resonance Spectroscopy / Q000379:methods* / Q000592:standards; D008956:Models, Chemical; D008968:Molecular Conformation; D011789:Quantum Theory; D012015:Reference Standards; D012680:Sensitivity and Specificity; D012717:Sesquiterpenes / Q000737:chemistry* / Q000302:isolation & purification; D013237:Stereoisomerism
D000438:Alcohols; D012717:Sesquiterpenes; C521923:artarborol