A bioinspired approach to tri-nor-guaianes. synthesis of (-)-clavukerin A.
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.
Blay
Gonzalo
G
Departament de Química Orgànica, Facultat de Química, Universitat de València, Dr. Moliner 50, E-46100, Burjassot, València, Spain.
García
Begoña
B
Molina
Eva
E
Pedro
José R
JR
D003508:Cycloheptanes / Q000737:chemistry*; D015394:Molecular Structure; D011084:Polycyclic Aromatic Hydrocarbons / Q000138:chemical synthesis* / Q000737:chemistry; D045789:Sesquiterpenes, Guaiane / Q000737:chemistry*; D013237:Stereoisomerism
D003508:Cycloheptanes; D011084:Polycyclic Aromatic Hydrocarbons; D045789:Sesquiterpenes, Guaiane; C473587:clavukerin A; C421026:guaiane