title: A bioinspired approach to tri-nor-guaianes. synthesis of (-)-clavukerin A.
abstract: A bioinspired approach to tri-nor-guaianes by degradation of the C-7 side chain of related guaia-11-enes is described. In this approach (-)-clavukerin A (1) is obtained by selective ozonolysis-Criegge rearrangement of (+)-1alphaH,7alphaH,10alphaH-guaia-4,11-dien-3-one (4) to afford 7beta-hydroxy and 7beta-acetoxy tri-nor-guaiane derivatives 6 and 7, respectively, which after elimination and deoxygenation give the title compound. The starting guaiadienone is readily obtained from commercially available santonin or (+)-dihydrocarvone.
authors.affiliation: Departament de Química Orgànica, Facultat de Química, Universitat de València, Dr. Moliner 50, E-46100, Burjassot, València, Spain.
authors.forename: Gonzalo
authors.initials: G
authors.lastname: Blay
authors.forename: Begoña
authors.initials: B
authors.lastname: García
authors.forename: Eva
authors.initials: E
authors.lastname: Molina
authors.forename: José R
authors.initials: JR
authors.lastname: Pedro
mesh_terms: D003508:Cycloheptanes / Q000737:chemistry*; D015394:Molecular Structure; D011084:Polycyclic Aromatic Hydrocarbons / Q000138:chemical synthesis* / Q000737:chemistry; D045789:Sesquiterpenes, Guaiane / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D003508:Cycloheptanes; D011084:Polycyclic Aromatic Hydrocarbons; D045789:Sesquiterpenes, Guaiane; C473587:clavukerin A; C421026:guaiane