The Chemistry of the Natural Order Cupressales. 45. The Structure and Configuration of Totarol and Totarolone.

Abstract

Totarolone, a constituent of the heartwood of Tetraclinis articulata has been reduced to the alcohol totaradiol and to totarol. The alcoholic hydroxyl group of the former compound is situated at C3. Totarol has been degraded to the dicarboxylic acid (10) also obtained from dehydroabietic acid. The structure and absolute configuration of totarolone are therefore represented by formula (la). A totarol analogue of xanthoperol and some similar compounds have been prepared from totarol.