Iodine(V) Reagents in Organic Synthesis. Part 2. Access to Complex Molecular Architectures via Dess−Martin Periodinane-Generated o-Imidoquinones
- 16 February 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 124 (10) , 2221-2232
- https://doi.org/10.1021/ja012125p
Abstract
o-Imidoquinones, a rather rare class of compounds, are prepared from anilides by the action of Dess−Martin periodinane (DMP) and water. Their chemistry has been extensively investigated and found to lead to p-quinones and polycyclic systems of diverse molecular architectures. Applications of this methodology to the total synthesis of the naturally occurring compounds, epoxyquinomycin B and BE-10988, are described. Finally, another rare chemical entity, the ketohydroxyamide moiety, has been accessed through this DMP-based synthetic technology, and its reactivity has been studied. Among its most useful reactions is a set of cascade heterocyclic annulations leading to a variety of polycyclic systems of possible biological relevance.Keywords
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