1,5-Diketones from 3,4-dihydropyranones: An application in the synthesis of (±)-α-herbertenol
✍ Scribed by David C. Harrowven; Joanne C. Hannam
- Book ID
- 108379394
- Publisher
- Elsevier Science
- Year
- 1999
- Tongue
- French
- Weight
- 750 KB
- Volume
- 55
- Category
- Article
- ISSN
- 0040-4020
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The paper describes a short synthesis of oc-herbertenol. Key features are the addition of dihyropyranone 5 to an aryllithium to give 1,5-diketone 7; a titanium(0) mediated cyclisation of 7 to diol8and asequentialmethylation of 8 toherbertenol methyl ether 9.
Featuring the Use of a Dihydropyranone as a 1,5-Diketone Synthon. -A short synthesis of the antifungally active sesquiterpene α-herbertenol (VII) is described. Key steps are the addition of an aryllithium reagent to dihydropyranone (II), which is used as 1,5-diketone synthon, and a titanium promote