Eine neue Methode zur stereochemischen Analyse offenkettiger terpenoider Carbonyl‐Verbindungen,

A New Method for the Stereochemical Analysis of Acyclic Terpenoid Carbonyl Compounds A new method for the determination of the enantiomeric and diastereoisomeric composition of terpenoid carbonyl compounds is presented. Separation of the diastereoisomeric (+)‐ L ‐diisopropyl‐tartrate acetals derived from dihydrocitronellal ( 6 ), hexahydropseudoionone ( 3 ), hexahydrofarnesal ( 7 ), and hexahydro far nesy lace tone ( 4 ), the C 10 , C 13 , C 15 , and C 18 intermediates in various syntheses of naturally occurring tocopherols and vitamin K 1 , can be achieved by capillary GC on a cyanopropylsilicon‐coated glass column under standardized conditions. This technique, presenting a significant improvement 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%, 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.