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- Title
A Chemical Study of Burley Tobacco Flavour (Nicotiana tabacum L.). III. Structure Determination and Synthesis of 5-(4-Methyl-2-furyl)-6-methylheptan-2-one (' Solanofuran') and of 3,4,7-Trimethyl-1,6- dioxa-spiro[4.5]dec-3-en-2-one ('Spiroxabovolide'), Two New Flavour Components of Burley Tobacco
- Authors
Demole, E.; Demole, C.; Berthet, D.
- Abstract
Two novel constituents of Burley tobacco condensate were shown to be 5-(4-methyl-2-furyl)-6-methylheptan-2-one ( solanofuran, 4) and 3,4,7-trimethyl-1,6-dioxa-spiro[4.5]-dec-3-en-2-one ( spiroxabovolide, 6). These structures were deduced from spectral data and confirmed by synthesis. Solanofuran ( 4) was prepared via the dye-sensitized photo-oxygenation of solanone ( 1). This type of reaction involving the uncommon 'diene-addition' of 1O2 to a conjugated acyclic diene system was thus applied for the first time to the synthesis of a terpenoid furan, a route that might have some biogenetic significance. Both solanofuran ( 4) and spiroxabovolide ( 6) display interesting organoleptic properties. Identification of these compounds increases to 210 the total number of Burley tobacco flavour constituents so far characterized in this laboratory.
- Publication
Helvetica Chimica Acta, 1973, Vol 56, Issue 1, p265
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19730560116