SYNTHESIS OF (-AROMADENDRENE DERIVATIVE S AS PHYSIOLOGICALLY ACTIVE SUBSTANCES())

(+)-Aromadendrene 1 was converted to derivatives by hydration with for mic acid, addition of an alcohol (methanol, ethanol, or 1-propanol) in the presence of a synthetic zeolite, or oxidation with lead tetraacet ate. Hydration of 1 with formic acid in the presence of 3 A zeolite ga ve (+)-globulol 5 as at least 68.2% of the hydration product. With 202 0 AH zeolite, the addition of an alcohol to 1 gave (+)-10-alcoxy aroma dendranes 6-8 as the main products. Oxidation of 1 with lead tetraacet ate gave (+)-aromadendrane-10, 14-diol 10 in a high yield (72.4%). Dio l 10 was treated in a pyridinium dichromate solution to gave the corre sponding ketone 11. This compound was a useful intermediate for furthe r synthesis, and was condensed with ethylene glycol, 1,2-ethanedithiol , or 1,3-propanedithiol to gave acetal compounds 12-14. Compounds 5 an d 12 inhibited the growth of Bacillus subtilis and Staphylococcus aure us.