ISSN:
0947-3440
Keywords:
Dracunculifoliol
;
Eudesmanes, 8(7→6)-abeo-
;
Vassoura oil
;
Baccharis dracunculifolia
;
Terpenes
;
Hydrindane Derivatives
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The cis-aldehyde 9, a key intermediate in the total synthesis of cis-dracunculifoliol (1) previously isolated from Vassoura oil, was prepared starting from the bicyclic enone 5 via the nitrile 8. Grignard reaction of 9 led exclusively to epi-1. Oxidation to the ketone 10 followed by reduction gave a separable mixture of the natural isomer 1 and epi-1. - The synthesis of trans-dracunculifoliol (2) starts with the 6-methoxytetralone 14. After some usual steps, the trans-octalin 17 was obtained. MMPP-HIO4 oxidation gave compound 19 which was transformed into the iodo ester 26, precursor of the hydrindane ester 27. Analogously to the synthesis of epi-1 the epi-trans-dracunculifoliol (epi-2) was formed via alcohol 28 and aldehyde 29. Oxidation ( 30) and reduction furnished the natural trans alcohol 2. - Olfactory evaluation of the purified isomers 1, epi-1, 2, and epi-2 showed that all of them possess only a weak, woody odor. Therefore, the dracunculifoliols 1 and 2 are not responsible for the typical earthy, leathery, and spicy odor of the Vassoura oil.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199519950233
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