alpha,beta-Unsaturated Diazoketones as Platforms in the Asymmetric Synthesis of Hydroxylated Alkaloids. Total Synthesis of 1-Deoxy-8,8a-diepicastanospermine and 1,6-Dideoxyepicastanospermine and Formal Synthesis of Pumiliotoxin 251D

Autor(es)

Bernardim, Barbara ^[1] ; Pinho, Vagner 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 Científico
• Fonte: Journal of Organic Chemistry; v. 77, n. 21, p. 9926-9931, NOV 2 2012.
• Citações Web of Science: 25

Resumo

A versatile and concise approach for the stereoselective synthesis of mono-, di-, and trihydroxylated indolizidines is presented in four to six steps from Cbz-prolinal and a diazophosphonate. The key steps involved a Wolff rearrangement, followed by a stereoselective dihydroxylation/epoxidation reaction, from an alpha,beta-unsaturated diazoketone. The strategy also permits extension to the synthesis of many natural hydroxylated indolizidine alkaloids as demonstrated in the formal synthesis of pumiliotoxin 251D. (AU)

• Processo FAPESP: 12/04685-5 - Novas metodologias sintéticas para a construção de sistemas pirrolidínicos, piperidínicos e indolizidínicos
• Beneficiário: Antonio Carlos Bender Burtoloso
• Modalidade de apoio: Auxílio à Pesquisa - Regular
• Processo FAPESP: 08/09653-9 - Síntese total dos cardiotônicos pumiliotoxina 209 F e homopumiliotoxina 223 G
• Beneficiário: Vagner Dantas Pinho
• Modalidade de apoio: Bolsas no Brasil - Doutorado