Tetrahedron p. 7237 - 7246 (1990)
Update date:2022-08-04
Topics:
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
(-)-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.
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