Diterpenes from Colophospermum mopane: "missing links" in the biogenesis of 9,13-epoxylabdanes.
Moponeol A (1) and moponeol B (2) were isolated from Colophospermum mopane along with a mixture of their corresponding aldehydes (3 and 4). These substances are primitive diterpenes that we view as the "missing links" in the biosynthesis of the 9,13-epoxylabdanes. The structures of 1 and 2 were elucidated by a combination of spectra (NMR and MS) of the isolates and their mono-p-bromobenzoyl derivatives. The structures of 3 and 4 were confirmed by their ready reduction to 1 and 2. The biosynthetic implications of the stereochemical assignments of these terpenoids are briefly discussed.
Reiter
Emily
E
Department of Chemistry and Biochemistry, University of Alaska Fairbanks, Fairbanks, Alaska 99775-6160, USA
Treadwell
Edward
E
Cederstrom
Ericka
E
Reichardt
Paul B
PB
Clausen
Thomas P
TP
D000447:Aldehydes / Q000737:chemistry* / Q000302:isolation & purification*; D004224:Diterpenes / Q000737:chemistry* / Q000302:isolation & purification*; D004951:Esterification; D007887:Fabaceae / Q000737:chemistry*; D013058:Mass Spectrometry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism; D015030:Zimbabwe
D000447:Aldehydes; D004224:Diterpenes; C474002:moponeol A; C474003:moponeol B