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RESEARCH PRODUCT
A Bioinspired Approach to Tri-nor-guaianes. Synthesis of (−)-Clavukerin A
Gonzalo BlayB. GarciaEva MolinaJosé R. Pedrosubject
PharmacologyOzonolysisMolecular StructureOrganic ChemistryPharmaceutical ScienceStereoisomerismSesquiterpeneChemical synthesisAnalytical ChemistrySesquiterpenes Guaianechemistry.chemical_compoundComplementary and alternative medicinechemistryDrug DiscoverySide chainMolecular MedicineOrganic chemistryCycloheptanesPolycyclic Aromatic HydrocarbonsEnantiomerSelectivityDeoxygenationdescription
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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2006-07-15 | Journal of Natural Products |