학술논문

The chemistry of thujone. XVI. Versatile and efficient routes to safronitrile, β-cyclogeranonitrile, β-cyclocitral, damascones, and their analogues
Document Type
Article
Source
Canadian Journal of Chemistry; July 1992, Vol. 70 Issue: 7 p2094-2114, 21p
Subject
Language
ISSN
00084042; 14803291
Abstract
Thujone, a waste by-product of the Canadian forest industry, has been utilized as a starting material to develop a versatile synthetic route to the damascones (rose oil ketones) and related analogues. The synthetic sequence provides a route to β-cyclocitral (45), the latter having been previously converted to β-damascone (2). In addition, thujone-derived intermediates are converted to β-damascenone (48) and to intermediates that can be utilized for the preparation of damascone analogues. In conjunction with the above, an efficient route to safronitrile (42), β-cyclogeranonitrile (43), and β-cyclocitral (45) from 2,6-dimethylcyclohexanone has been developed. In summary, these studies afford an attractive versatile route to these important perfumery materials.