Contribution a l'etude des composes sesquiterpeniques—IV

Transformation of Carotol into the Hydroindane-Derived Musk Odorant

“…[ Ozonolysis of carotol (1) in acetic acid followed by a Zn/ AcOH reduction according to a modified method [9,10] delivered dihydroxy ketone 2 in 63% yield, as a result of spontaneous intramolecular condensation of the intermediate oxo aldehyde. [11,12] Structure 2 was established earlier [4,11] but the stereochemistry of its new stereogenic centres was unknown. The compound was then purified by crystallisation from toluene to give large, white crystals and the absolute configuration of its chiral atoms as R C1 ,R C4 ,S C5 ,S C7 ,S C8 was determined by X-ray crystallography.…”

Chemistry of the Carotane Sesquiterpenes V. Biosimulated Conversions

“…In the presence of Pd C at 3 atm hydrogen pressure, daucene gave 15, 16 and daucane (18). Daucane was also obtained, as previously described (22). by hydrogenation of carotol.…”

“…Thus one observes a 1:1 ratio of epoxide isomers. On treatment with 90% formic acid or stannic chloride in benzene, both 22 and 23 gave complex mixtures: these procedures, therefore, did not seem a viable method of converting the carotane skeleton into the acorane skeleton.…”

Dialkoxycarbenes in (4 + 1) Cycloadditions: Application to the Synthesis of Carotol

“…(+)-Carotol ( 1 ) is a daucane-type sesquiterpene found in the seeds and roots of many plants of the Apiaceae (carrots) and Zingiberaceae (ginger) families . Controversy existed around its structure for a while, but it was eventually proven by Šorm in 1959 . It has strong larvicidal and antimicrobial activities and acts as a potent olfactive attractant to the black bean aphid (Aphis fabae)…”