Juvenile Hormone Analogs in Conifers. II. Isolation, Identification, and Biological Activity of cis-4-[1′(R)-5′-Dimethyl-3′-oxohexyl]-cyclohexane-1-carboxylic Acid and (+)-4(R)-[1′(R)-5′-Dimethyl-3′-oxohexyl]-1-cyclohexene-1-carboxylic Acid from Douglas-fir Wood

The petroleum ether extract from the whole-wood meal of a number of British Columbia Interior-Intermediate variety Douglas-fir trees have yielded two carboxylic acids (+)-todomatuic acid (3b) and cis-dihydrotodomatuic acid (4b) which as their methyl esters are potentially useful juvenile hormone analogs. These compounds possess the R,R and R stereoconfigurations, respectively. The configuration at C-1′ is opposite to that reported by others for "(+)-juvabione" isolated from Abiesbalsamea grown in Czechoslovakia. Whereas (+)-juvabione naturally occurs as and is the methyl ester of (+)-todomatuic acid (4b), in this variety of Douglas-fir these compounds appear as the free acids. Results of biological assays on certain insects indicate that the methyl ester derivatives of these acids are effective ovicides and juvenilizing hormones.