Biosynthesis of the abietane type diterpene ferruginol in cell cultures of Salvia miltiorrhiza: synthesis of (15S)- and (15R)-[16-2H1]12-O-methylferruginol by enzymatic resolution of 12-O-methyl-16-hydroxyferruginol and stereochemistry of 1,2-methyl migration in the formation of the isopropyl group

Abstract

The signals for the pro(R) and pro(S) methyl groups of the isopropyl group, in the ¹³C{¹H} n.m.r. spectrum of 12-O-methylferruginol, have been assigned by the synthesis of the title compounds and the stereochemistry of 1,2-methyl migration for biosynthesis of the abietane skeleton of ferruginol has been established.