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

✍ Scribed by Thommen, Christophe; Jana, Chandan Kumar; Neuburger, Markus; Gademann, Karl

Book ID: 120019110
Publisher: American Chemical Society
Year: 2013
Tongue: English
Weight: 445 KB
Volume: 15
Category: Article
ISSN: 1523-7060
DOI: 10.1021/ol4003652

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✦ Synopsis

A protecting-group-free route to (À)-taiwaniaquinone F based on a ring contraction and subsequent aromatic oxidation of a sugiol derivative is reported. In addition, the first synthesis of (þ)-taiwaniaquinol A is reported via short time exposure of (À)-taiwaniaquinone F to sunlight triggering a remote CÀH functionalization. The hypothesis that the biogenesis of some methylenedioxy bridged natural products could proceed via similar nonenzymatic mechanisms is presented.

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