The constitution of Gmelinol. III. Final elucidation

Abstract

Reduction of gmelinol (I) with sodium and ethanol in liquid ammonia gives the trio1 (III), the constitution of which is confirmed by oxidation with lead tetra-acetate to produce formaldehyde. Eudesmin (VIII) by a similar reduction gives rise to the enantiomer of the known diol (IX), galgravin (X) gives rise to XI, and 3,4-dimethoxy-benzyl decyl ether produces 3,4-dimethoxytoluene.