Einfache Synthese von 6-[4-Methyl-3-cyclohexen-1-yl]-hept-5-en-2-on, einer Vorstufe für α-Bisabolen und dessen Isopropenyl-Isomers. Terpene und Terpen-Derivate, 10. Mitteilung
✍ Scribed by Manfred Becker; Peter Weyerstahl
- Publisher
- John Wiley and Sons
- Year
- 1979
- Tongue
- German
- Weight
- 392 KB
- Volume
- 62
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Simple Synthesis of 6‐[4‐Methyl‐3‐cyclohexen‐1‐yl]‐5‐hepten‐2‐on, a Precursor of α‐Bisabolene and Its Isopropenyl Isomer
The alcohol 14 reacts with vinyl resp isopropenyl ether by Claisen rearrangement to give the aldehyde 16/17 resp. the ketone 3/4. Contrary to other reports this separable (E/Z)‐mixture also occurs as a result of the synthesis following the pathway 7 → 8/9 → 10/11 → 12/13 (see also [2]). The bisabolene isomers 5 resp. 6 are obtained by reaction of 3 resp. 4 with methylidene triphenyl phosphorane. A mixture of 1 and 5. however, is formed from 3 via the alcohol 18 and its acetate 19. Likewise 4 reacts via 20 and 21 to give a (2/6)‐mixture.