Volume 31, Issue 51
Natural Products
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ChemInform Abstract: Oxazolium-Derived Azomethine Ylides. External Oxazole Activation and Internal Dipole Trapping in the Synthesis of an Aziridinomitosene.

Edwin Vedejs

Edwin Vedejs

Dep. Chem., Univ. Mich., Ann Arbor, MI 48109, USA

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David W. Piotrowski

David W. Piotrowski

Dep. Chem., Univ. Mich., Ann Arbor, MI 48109, USA

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Fabio C. Tucci

Fabio C. Tucci

Dep. Chem., Univ. Mich., Ann Arbor, MI 48109, USA

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First published: 31 May 2010

Abstract

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ChemInform Abstract

It is shown that benzylated aziridine derivatives of type (IV) can be selectively alkylated at the oxazole nitrogen yielding salts like (VI). Treatment of the latter with Bn-NMe3CN gives azomethine ylides [see (VII)] which undergo cycloaddition forming indoles like (VIII). Interestingly, under these conditions the aziridine ring remains intact. (VIII) can smoothly be transformed into the aziridinomitosene derivative (XI).

chemical structure image

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