An asymmetric substrate-controlled Morita-Baylis-Hillman reaction as approach for the synthesis of pyrrolizidinones and pyrrolizidines

Autor(es)

Luna-Freire, Kristerson R. ^[1] ; Scaramal, Joao Paulo S. ^[1] ; Resende, Jackson A. L. C. ^[2] ; Tormena, Claudio F. ^[3] ; Oliveira, Fabio L. ^[4] ; Aparicio, Ricardo ^[4] ; Coelho, Fernando ^[1]

Afiliação do(s) autor(es)

^[1] Univ Estadual Campinas, Inst Chem, Lab Synth Nat Prod & Drugs, BR-13083970 Campinas, SP - Brazil

^[2] Inst Quim UFF, Xray Diffract Lab, Niteroi, RJ - Brazil

^[3] Univ Estadual Campinas, Inst Chem, Lab Phys Organ Chem, BR-13083970 Campinas, SP - Brazil

^[4] Univ Estadual Campinas, Inst Chem, Lab Struct Biol & Crystallog, BR-13083970 Campinas, SP - Brazil

• Tipo de documento: Artigo Científico
• Fonte: Tetrahedron; v. 70, n. 20, p. 3319-3326, MAY 20 2014.
• Citações Web of Science: 5

Resumo

We describe herein an approach to the total synthesis of functionalized pyrrolizidinones and pyrrolizidines. The synthetic sequence is based on a highly stereoselective substrate-controlled Morita-Baylis-Hillman (MBH) reaction between a chiral amino-aldehyde and methyl acrylate. The selectivity attained in this reaction was controlled by the presence of a hydroxyl group adequately placed in the structure of the amino-aldehyde used as the nucleophilic component of the MBH reaction. The MBH adducts were used as substrate for an efficient total synthesis of pyrrolizidinones and pyrrolizidines in good overall yield. (C) 2013 Elsevier Ltd. All rights reserved. (AU)

• Processo FAPESP: 09/51602-5 - Biologia química: novos alvos moleculares naturais e sintéticos contra o câncer, estudos estruturais, avaliação biológica e modo de ação
• Beneficiário: Ronaldo Aloise Pilli
• Modalidade de apoio: Auxílio à Pesquisa - Temático
• Processo FAPESP: 11/20033-5 - Síntese de heterociclos utilizando adutos de Morita-Baylis-Hillman
• Beneficiário: Fernando Antonio Santos Coelho
• Modalidade de apoio: Auxílio à Pesquisa - Regular