132842-97-8Relevant articles and documents
The conversion of natural (+)-aromadendrene into chiral synthons-I
Gijsen, Henricus J. M.,Kanai, Karoly,Stork, Gerrit A.,Wijnberg, Joannes B.P.A.,Orru, Romano V. A.,Seelen, Claudy G. J. M.,Van Der Kerk, Sies M.,De Groot, Aede
, p. 7237 - 7246 (2007/10/02)
(-)-Apoaromadendrone (3) can be obtained easily in large quantities from (+)-aromadendrene which is the main constituent in a commercially available distillation tail of the oil of Eucalyptus globules. Acid catalyzed selective cleavage of the C3-C4 bond of the cyclopropane ring in 3 gave (-)-isoapoaromadendrone(9) in high yield. The regioselectivity of the cyclopropane ring opening was proved by NMR spectroscopy in combination with chemical transformations. Ozonolysis of 9 afforded the keto alcohol 14 which is a suitable chiral intermediate for the syntheses of guaianes and guaianolides.