Issue 18, 2011
From the journal:

Organic & Biomolecular Chemistry

1,3-Dipolar cycloadditions from tricyclic hemiaminals. Synthesis of the quinocarcin core through catalyst-free generation of azomethine ylides†

Lena Huck,a   J. Francisco González,a   Elena de la Cuesta,a   J. Carlos Menéndeza  and  Carmen Avendaño*a  

* Corresponding authors

a Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense, Plaza Ramón y Cajal s/n, 28040 Madrid, Spain
E-mail: avendano@farm.ucm.es

Abstract

The generation of azomethine ylides from the readily accessible hemiaminals 3 and 8 or from iminium salt 10 was studied. Compounds 8 gave anti- and syn-cycloadducts containing the quinocarcin core through a catalyst-free dehydration process.

Graphical abstract: 1,3-Dipolar cycloadditions from tricyclic hemiaminals. Synthesis of the quinocarcin core through catalyst-free generation of azomethine ylides

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Article information

DOI
https://doi.org/10.1039/C1OB05181D
Article type
Paper
Submitted
01 Feb 2011
Accepted
08 Jun 2011
First published
08 Jun 2011

Org. Biomol. Chem., 2011,9, 6271-6277

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1,3-Dipolar cycloadditions from tricyclic hemiaminals. Synthesis of the quinocarcin core through catalyst-free generation of azomethine ylides

L. Huck, J. F. González, E. de la Cuesta, J. C. Menéndez and C. Avendaño, Org. Biomol. Chem., 2011, 9, 6271 DOI: 10.1039/C1OB05181D

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