ISSN:
0947-3440
Keywords:
Tricyclic sesquiterpenes
;
Italicene derivatives
;
α-Copaene derivatives
;
Essential oils
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Oxidation of the tricyclic sesquiterpene hydrocarbon italicene (1a) or its 10-epimer 1b (isolated previously from Helichrysum oil) with SeO2 yielded mixtures of italicene-5-one (3a), italicen-15-al (4a), italicen-5-ol (9a) and italicen-15-ol (10a) or their 10-epimers 3b, 4b, 9b, 10b, whereas commercial α-copaene (6) reacted only to give a mixture of α-copaen-15-al (7) and α-copaen-15-ol (8). Jones oxidation of the allyl alcohols 9a or 9b afforded the pure ketones 3a or 3b MnO2 oxidation of the alcohols 10a or 10b furnished the aldehydes 4a or 4b. - Surprisingly, the italicene epoxides 2a or 2b rearranged with diluted HCl to the italicene ethers (epoxyacorenes) 5a or 5b, which previously were isolated from Lantana and Helichrysum oil. - The odor of 3a, 3b, 4a, 4b and 5a was evaluated.
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199619961022
