Stereochemistry of C-methylation in the biosynthesis of rhododendrin in Alnus and Betula

Klischies, Martina and Zenk, Meinhart H. (1978): Stereochemistry of C-methylation in the biosynthesis of rhododendrin in Alnus and Betula. In: Phytochemistry, Vol. 17, No. 8: pp. 1281-1284

Abstract

Using differently labelled precursors, it was established that rhododendrin (3-(4-hydroxyphenyl)-1-methylpropyl-β- -glucopyranoside) is formed through the phenylpropane pathway via p-coumaryl alcohol, dihydro-p-coumaryl alcohol and C-methylation of the γ-C-atom of the C6---C3 unit with methionine supplying the methyl group. It was demonstrated that the pro-(S)-hydrogen atom of dihydro-p-coumaryl alcohol is replaced stereospecifically by the methyl group.

• Item Type: Article
• Keywords: Betula alba; Alnus glutinosa; Betulaceae; cinnamic acid pathway; C-methylation; stereochemistry; rhododendrin; phenylpropanoid
• Collections: Chemistry and Pharmacy
• Subjects: 500 Science > 540 Chemistry