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Syntheses of Taiwaniaquinone F and Taiwaniaquinol A via an Unusual Remote C-H Functionalization

Thommen, Christophe and Jana, Chandan Kumar and Neuburger, Markus and Gademann, Karl. (2013) Syntheses of Taiwaniaquinone F and Taiwaniaquinol A via an Unusual Remote C-H Functionalization. Organic letters, Vol. 15, H. 6. pp. 1390-1393.

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Official URL: http://edoc.unibas.ch/dok/A6223301

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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.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Former Organization Units Chemistry > Organische Chemie (Gademann)
UniBasel Contributors:Gademann, Karl
Item Type:Article, refereed
Article Subtype:Research Article
Bibsysno:Link to catalogue
Publisher:American Chemical Society
ISSN:1523-7060
Note:Publication type according to Uni Basel Research Database: Journal article
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Last Modified:27 Feb 2014 15:46
Deposited On:27 Feb 2014 15:46

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