Abstract

(+)-Aromadendrene 1 was converted to derivatives by hydration with formic acid, addition of an alcohol (methanol, ethanol, or 1-propanol) in the presence of a synthetic zeolite, or oxidation with lead tetraacetate. Hydration of 1 with formic acid in the presence of 3 A zeolite gave (+)-globulol 5 as at least 68.2% of the hydration product. With 2020 AH zeolite, the addition of an alcohol to 1 gave (+)-10-alcoxy aromadendranes 6-8 as the main products. Oxidation of 1 with lead tetraacetate gave (+)-aromadendrane-10, 14-diol 10 in a high yield (72.4%). Diol 10 was treated in a pyridinium dichromate solution to gave the corresponding ketone 11. This compound was a useful intermediate for further synthesis, and was condensed with ethylene glycol, 1, 2-ethanedithiol, or 1, 3-propanedithiol to gave acetal compounds 12-14. Compounds 5 and 12 inhibited the growth of Bacillus subtilis and Staphylococcus aureus.

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