Recherches sur les arǒmes. 17e communication. Sur l'arǒme de framboise, IV

✍ Scribed by M. Winter; P. Enggist

• Publisher: John Wiley and Sons
• Year: 1971
• Tongue: German
• Weight: 395 KB
• Volume: 54
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19710540717

✦ Synopsis

NMR. spectrum shows the presence of three quarternary methyl groups with a fourth methyl group attached to a double bond. The methylvinylfuran part of the davanone NMR. spectrum1) is almost unchanged, so we formulated a working hypothesis of different isomers of structure 3 as representing the isomeric mixture. 4 3

This was confirmed by the following synthesis. Davanone was epoxidized with peroxyacetic acid in methylene chloride, and the epoxide 4 was treated for 38 h with Dowex 50 ion-exchange resin (H+-form) in absolute ether, when ring opening of the epoxide occurred with participation of the carbonyl group and dehydration to yield a mixture of isomers having the same retention time on gas chromatography, the same thin-layer chromatographic characteristics, and the same spectra as the natural mixture.

Further details of these compounds and their synthesis will be published in due course.