No abstract

Exo-and Endohormones.Part 17. Synthesis of Racemic 5,9-Dimethyl-heptadecane, the Sex Pheromone for the Leafminer Moth Leucoptera scitella.-Two alternative routes for the synthesis of the title compound (VIII) based on C 9 + C 8 or C 6 + C 11 Grignard coupling reactions are described. -(CIOCAN-TARTA, I.; OPREAN, I.; GHIZDAVU, I.; POJAR-FENESAN, M.; Rev. Roum. Chim. 43 (1998) 3, 215-219; "Raluca Ripan" Inst. Chem., RO-3400 Cluj-Napoca, Rom.; EN)

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

(8S)‐(−)‐p‐Mentha‐1,3‐dien‐9‐ol (3) has been synthesized and fully characterized, using dill ether as the starting material. Dill ether is a common constituent of the essential oil of dill weed, Anethum graveolens L. In the first step, (8S)‐(−)‐p‐mentha‐1,3‐dien‐9‐yl acetate was prepared by treating dill ether with anhydrous magnesium bromide, followed by the addition of acetic anhydride. Hydrolysis of this mixture with potassium hydroxide led to the formation of alcohol 3, with p‐cymen‐9‐ol as the main by‐product. The chemical identity of compound 3 has been confirmed by GC/MS, IR, one‐ and two‐dimensional NMR. Chiral analysis has shown that it consists of enantiomerically pure (8S)‐(−)‐p‐mentha‐1,3‐dien‐9‐ol. This has been corroborated by selective oxidation of p‐mentha‐1,3,8‐triene found in the essential oil of curly leaf parsley, Petroselinum crispum (Mill.) Fuss., to give a racemic mixture of p‐mentha‐1,3‐dien‐9‐ol. Other esters (propionate, butyrate and valerate) of alcohol 3 have been prepared in a similar way by treating dill ether with the corresponding acid anhydride. Olfactory evaluation of alcohol 3 revealed a floral character while its esters gave a range of fruity and herbaceous notes.