The Allylic Oxidation of Geraniol Catalyzed by Cytochrome P-450Cath., Proceeding with retention of configuration

Incubation of the geraniols (R)-(8-²H₁)8-³H₁]- 1 and (S)-(8-²H₁)8-³H₁]- 1 with microsomal cytochrome P-450_Cath. from the subtropical plant Catharanthus roseus (L.)G. DON resulted in the formation of the chiral 8-hydroxygeraniols (S)-(8-²H₁)8-³H₁]- 2 and (R)-(8-²H₁)8-³H₁]- 2 . Their absolute configuration was assigned on the basis of the ¹H-decoupled ³H-NMR Spectra of the corresponding dicamphanates (S)-(8-²H₁)8-³H₁]- 9 and (R)-(8-²H₁)8-³H₁]- 9 , of which the configurations are established in relation to the synthetic reference samples. The results clearly indicate retention of configuration during the allylic oxidation of 1 .