Constituents of Erythroxylon monogynum Roxb. Part I. (+)-Hibaene, [(+)-stachene], erythroxylol A (monogynol), erythroxylol B, and erythroxydiol A

Abstract

The constitution and stereochemistry of (+)-hibaene (2), erythroxylol A (3), erythroxylol B (8), and erythroxydiol A (11) is assigned on the basis of their spectroscopic properties and chemical reactions. Erythroxydiol A has been converted into erythroxylol A, and both erythroxylol A and B have been converted into (+)-hibaene. The relationship of the double bond and primary alcohol functions in erythroxylol B has been determined by oxidative cleavage. A study of the hydroboration products from erythroxylol A has been made.