Determination of the absolute stereochemistry of the epoxide group in alpinia epoxide by NMR

Determination of the absolute stereochemistry of the epoxide group in alpinia epoxide by NMR

The absolute stereochemistry of the epoxide group in alpinia epoxide [14,15-epoxylabda-8(17),12-dien-16-al ( E)] has been determined by simultaneous reduction of the aldehyde and epoxide functional groups in this molecule to primary and secondary alcohols, followed by selective protection of the pri...

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Veröffentlicht in:Phytochemistry (Oxford) 1998-11, Vol.49 (6), p.1741-1744
Hauptverfasser: Sy, Lai-King, Brown, Geoffrey D.
Format: Artikel
Sprache:eng
Schlagworte:
14,15-epoxylabda-8,12-dien-16-al ( E)
absolute stereochemistry
alcohols
aldehydes
alpina epoxide
Alpinia
Alpinia chinensis
Biological and medical sciences
chemical constituents of plants
Chemical constitution
chemical reactions
chemical structure
epoxides
esters
Fundamental and applied biological sciences. Psychology
Mosher ester, two-dimensional NMR
nuclear magnetic resonance spectroscopy
Plant physiology and development
S(+)/R(−) MTPCl
spectral analysis
Zingiberaceae
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Zusammenfassung:The absolute stereochemistry of the epoxide group in alpinia epoxide [14,15-epoxylabda-8(17),12-dien-16-al ( E)] has been determined by simultaneous reduction of the aldehyde and epoxide functional groups in this molecule to primary and secondary alcohols, followed by selective protection of the primary alcohol and derivitization of the secondary alcohol with S(+) and R(−) MTPCl as Mosher esters. Changes in 1H NMR chemical shifts for all positions in these two esters were determined by 2D-NMR and used to infer the absolute stereochemistry of the epoxide group in the natural product alpinia epoxide.
ISSN:0031-9422
1873-3700
DOI:10.1016/S0031-9422(98)00298-2