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

Abstract

Abstract Incubation of the geraniols ( R )‐(8‐ 2 H 1 )[8‐ 3 H 1 ]‐ 1 and ( S )‐(8‐ 2 H 1 )[8‐ 3 H 1 ]‐ 1 with microsomal cytochrome P‐450 Cath. from the subtropical plant Catharanthus roseus (L.)G. D ON resulted in the formation of the chiral 8‐hydroxygeraniols ( S )‐(8‐ 2 H 1 )[8‐ 3 H 1 ]‐ 2 and ( R )‐(8‐ 2 H 1 )[8‐ 3 H 1 ]‐ 2 . Their absolute configuration was assigned on the basis of the 1 H‐decoupled 3 H‐NMR Spectra of the corresponding dicamphanates ( S )‐(8‐ 2 H 1 )[8‐ 3 H 1 ]‐ 9 and ( R )‐(8‐ 2 H 1 )[8‐ 3 H 1 ]‐ 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 .