The stereochemistry of ledol from Renealmia chrysotrycha: an NMR study.
From the leaves of Renealmia chrysotrycha (Zingiberaceae), we isolated a sesquiterpene alcohol for which spectral data suggested the structure of a 10-aromadendranol. A meticulous NMR investigation, based mainly on vicinal proton-proton coupling constants and NOE interactions, and confirmed by a molecular mechanics calculation, established its relative stereochemistry as that of ledol. This finding resolves several recent literature ambiguities. Three known compounds (aromadendrene, cis-calamenene and palustrol) were also isolated.
Kaplan
M A
MA
Nucleo de Pesquisa de Produtos Naturais, Universidade Federal do Rio de Janeiro, RJ, Brazil.
Pugialli
H R
HR
Lopes
D
D
Gottlieb
H E
HE
D009682:Magnetic Resonance Spectroscopy; D019684:Magnoliopsida / Q000737:chemistry*; D008958:Models, Molecular; D012717:Sesquiterpenes / Q000737:chemistry* / Q000302:isolation & purification; D013237:Stereoisomerism
D012717:Sesquiterpenes; C421806:ledol