Synthesis of diverse heterocyclic scaffolds via tandem additions to imine derivatives and ring-forming reactions |
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Authors: | James D Sunderhaus |
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Institution: | Department of Chemistry and Biochemistry, The Texas Institute for Drug and Diagnostic Development, The University of Texas at Austin, 1 University Station A5300, Austin, TX 78712-0165, USA |
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Abstract: | A novel strategy has been developed for the efficient syntheses of diverse arrays of heterocyclic compounds. The key elements of the approach comprise a Mannich-type, multicomponent coupling reaction in which functionalized amines, aromatic aldehydes, acylating agents, and π- and organometallic nucleophiles are combined to generate intermediates that are then further transformed into diverse heterocyclic scaffolds via a variety of cyclization manifolds. Significantly, many of these scaffolds bear functionality that may be exploited by further manipulation to create diverse collections of compounds having substructures found in biologically active natural products and clinically useful drugs. The practical utility of this strategy was exemplified by its application to the first, and extraordinarily concise synthesis of the isopavine alkaloid roelactamine. |
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Keywords: | Imine Acyliminium ion Multicomponent reaction Drug-like scaffolds Natural products Mannich reaction Heck reaction Ring-closing metathesis Alkaloids |
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