Helvetica Chimica Acta p. 1087 - 1107 (1990)
Update date:2022-08-04
Topics:
Knierzinger, Andreas
Walther, Willy
Weber, Beat
Mueller, Robert Karl
Netscher, Thomas
A new method for the determination of the enantiomeric and diastereoisomeric composition of terpenoid carbonyl compounds is presented.Separation of the diastereomeric (+)-L-diisopropyl-tartrate acetals derived from dihydrocitronellal (6), hexahydropseudoionone (3), hexahydrofarnesal (7), and hexahydrofarnesylacetone (4), the C10, C13, C15, and C18 intermediates in various syntheses of naturally occuring tocopherols and vitamin K1, can be achieved by capillary GC on a cyanopropylsilicon-coated glass column under standardized conditions.This technique, presenting a significant improvment over existing methodologies, is considered to be particularly useful for the analysis of highly enriched samples, typically obtained by present-day asymmetric synthesis.With reproducibilities of +/- 0.3 percent, and therefore, safe for routine analysis, the complete stereochemical characterization of terpenoids with 15 and 18 C-atoms bearing two stereogenic centres is performed in a single operation for the first time.
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