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

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

Journal Name: Current Topics in Medicinal Chemistry

Volume 13 , Issue 17 , 2013

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Abstract:

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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Article Details

VOLUME: 13
ISSUE: 17
Year: 2013
Page: [2099 - 2103]
Pages: 5
DOI: 10.2174/15680266113139990145
Price: $65

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