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

Autor(es)

Bernardim, Barbara ^[1] ; Lordello, Leonardo D. ^[1] ; Burtoloso, Antonio C. B. ^[1]

Afiliação do(s) autor(es)

^[1] Univ Sao Paulo, Inst Quim Sao Carlos, BR-13560970 Sao Carlos, SP - Brazil

• Tipo de documento: Artigo de Revisão
• Fonte: CURRENT TOPICS IN MEDICINAL CHEMISTRY; v. 13, n. 17, p. 2099-2103, SEP 2013.
• Citações Web of Science: 8

Resumo

A four-step approach for the synthesis of dihydroxylated piperidine, quinolizidine and indolizidine systems is described employing alpha,beta-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. (AU)

• Processo FAPESP: 12/04685-5 - Novas metodologias sintéticas para a construção de sistemas pirrolidínicos, piperidínicos e indolizidínicos
• Beneficiário: Antonio Carlos Bender Burtoloso
• Linha de fomento: Auxílio à Pesquisa - Regular