Studies on Monoterpene Glucosides and Related Natural Products. XLV. Synthesis of ¹³C-Labeled Acyclic Monoterpenes for Studies on the Mechanism of the Iridane Skeleton Formation in the Biosynthesis of Iridoid Glucosides

Abstract

For studies on the cyclopentane ring formation from acyclic monoterpenes in the biosynthesis of iridoid glucosides, the following ¹³C-labeled precursors of the acyclic monoterpene series were synthesized : [9-¹³C]-and [4-¹³C]-10-hydroxygeraniol (9), [2-¹³C]-9, 10-dihydroxygeraniol (10), (R)-(+)-and (S)-(-)-[9-¹³C]-10-hydroxycitronellol ((R)-(+)-and (S)-(-)-8), (R)-(+)-and (S)-(-)-[8-¹³C]-9, 10-dihydroxycitronellol ((R)-(+)-and (S)-(-)-11).