title: Syntheses of taiwaniaquinone F and taiwaniaquinol A via an unusual remote C-H functionalization.
abstract: A protecting-group-free route to (-)-taiwaniaquinone F based on a ring contraction and subsequent aromatic oxidation of a sugiol derivative is reported. In addition, the first synthesis of (+)-taiwaniaquinol A is reported via short time exposure of (-)-taiwaniaquinone F to sunlight triggering a remote C-H functionalization. The hypothesis that the biogenesis of some methylenedioxy bridged natural products could proceed via similar nonenzymatic mechanisms is presented.
authors: Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel, Switzerland.
authors: Christophe
authors: C
authors: Thommen
authors: Chandan Kumar
authors: CK
authors: Jana
authors: Markus
authors: M
authors: Neuburger
authors: Karl
authors: K
authors: Gademann
mesh_terms: D029779:Cupressaceae / Q000737:chemistry; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011809:Quinones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D004224:Diterpenes; D011809:Quinones; C501333:sugiol; C582266:taiwaniaquinol A; C556366:taiwaniaquinone F