Juvenile Hormone Mimics in Conifers. I. Isolation of (−)-cis-4-[1′(R)-5′-Dimethyl-3′-oxohexyl]-cyclohexane-1-carboxylic Acid from Douglas-fir Wood

Abstract

The petroleum ether extract from the whole-wood meal of a British Columbia Interior variety of Douglas-fir has yielded a new and potentially useful juvenile hormone mimic, (−)-cis-4-[1′(R)-5′-dimethyl-3′-oxohexyl]-cyclohexane-1-carboxylic acid (3a). This compound possesses the opposite steric configuration at C-1′ to that of (+)-juvabione (1a), which has been isolated by others from balsam fir. Also, it occurs exclusively as the free acid. Not all Douglas-firs contain this compound and the biological consequences of its formation are being explored.