A New Method for the Stereochemical Analysis of Acyclic Terpenoid Carbonyl Compounds

Article abstract of DOI:10.1002/hlca.19900730432

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.