ISSN:
1434-193X
Keywords:
Rearrangements
;
Ireland-Claisen reaction
;
Nerol
;
Odoriferous substances
;
Terpenes
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
(2Z,6E)-3,6-Dimethylocta-2,6-dien-1-ol (6) was synthesized by Steglich esterification of (2E)-2-methylbut-2-en-1-ol (tiglic alcohol, 7) with 3-methylbut-2-en-1-oic acid (senecioic acid, 8), followed by selective Ireland-Claisen rearrangement of the resulting ester 9 at 0°C and subsequent Cope rearrangement of the product at 140°C. A standard LAH reduction in the last step of the synthetic sequence transformed the α,β-unsaturated acid 12 into the target molecule 6, a constitutional isomer of nerol (5) with interesting olfactory properties.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
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