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Current Topics in Medicinal Chemistry


ISSN (Print): 1568-0266
ISSN (Online): 1873-4294

α,β-Unsaturated Diazoketones as Versatile Building Blocks for the Synthesis of Hydroxylated Piperidines, Indolizidines and Quinolizidines

Author(s): Barbara Bernardim, Leonardo D. Lordello and Antonio C.B. Burtoloso

Volume 13, Issue 17, 2013

Page: [2099 - 2103] Pages: 5

DOI: 10.2174/15680266113139990145

Price: $65


A four-step approach for the synthesis of dihydroxylated piperidine, quinolizidine and indolizidine systems is described employing α,β-unsaturated diazoketones as versatile building blocks. Unsaturated diazoketones were readily prepared from a Horner-Wadsworth-Emmons reaction between a diazophosphonate and amino-aldehydes. The strategy employs an asymmetric dihydroxylation reaction as the key step and is simple and straightforward enough to be extended to other nitrogen heterocycles.

Keywords: Diazocompounds, glucosidases, indolizidines, piperidines, quinolizidines, α, β-unsaturated diazoketones.

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