Issue 30, 2012
From the journal:

Organic & Biomolecular Chemistry

Synthesis of isoxazolesen route to semi-aromatized polyketides: dehydrogenation of benzonitrile oxide–para-quinone acetal cycloadducts†‡

Yoshimitsu Hashimoto,a   Akiomi Takada,a   Hiroshi Takikawaa  and  Keisuke Suzuki*a  

* Corresponding authors

a Department of Chemistry, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo 152-8551, Japan
E-mail: ksuzuki@chem.titech.ac.jp
Fax: +03 5734 2788
Tel: +03 5734 2228

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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Article information

DOI
https://doi.org/10.1039/C2OB25423A
Article type
Paper
Submitted
27 Feb 2012
Accepted
03 Apr 2012
First published
18 May 2012

Org. Biomol. Chem., 2012,10, 6003-6009

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Synthesis of isoxazoles en route to semi-aromatized polyketides: dehydrogenation of benzonitrile oxide–para-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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