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Issue 30, 2012
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Synthesis of isoxazoles en route to semi-aromatized polyketides: dehydrogenation of benzonitrile oxidepara-quinone acetal cycloadducts

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Abstract

A variety of highly functionalized polycyclic isoxazoles are prepared by a two-step protocol: (1) 1,3-dipolar cycloaddition of o,o′-disubstituted benzonitrile oxides to para-quinone mono-acetals, then (2) dehydrogenation. The cycloaddition proceeds in a regioselective manner, favouring the formation of the 4-acyl cycloadducts, which are suitable intermediates for the synthesis of semi-aromatized polycyclic targets derived from polyketide type-II biosynthesis.

Graphical abstract: Synthesis of isoxazoles en route to semi-aromatized polyketides: dehydrogenation of benzonitrile oxide–para-quinone acetal cycloadducts

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Publication details

The article was received on 27 Feb 2012, accepted on 03 Apr 2012 and first published on 18 May 2012


Article type: Paper
DOI: 10.1039/C2OB25423A
Citation: Org. Biomol. Chem., 2012,10, 6003-6009
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    Synthesis of isoxazoles en route to semi-aromatized polyketides: dehydrogenation of benzonitrile oxidepara-quinone acetal cycloadducts

    Y. Hashimoto, A. Takada, H. Takikawa and K. Suzuki, Org. Biomol. Chem., 2012, 10, 6003
    DOI: 10.1039/C2OB25423A

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