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An Improved and Versatile Method for the Rapid Synthesis of Aryldihydrobenzofuran Systems by a Boron Tribromide-Mediated Cyclization Reaction

✍ Scribed by Richard Detterbeck; Manfred Hesse

Publisher: John Wiley and Sons
Year: 2003
Tongue: German
Weight: 204 KB
Volume: 86
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.200390036

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✦ Synopsis

Abstract

Boron tribromide is presented as a highly reactive reagent that simultaneously allows the demethylation and fully diastereoselective cyclization of different precursor molecules, obtained by an aldol‐type reaction, to a series of hydroxylated aryldihydrobenzofuran systems in racemic form. The latter are often found as key structures in natural compounds of different classes. Syntheses of educts, which mainly took advantage of a versatile Rieche formylation, are also described.

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