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

Author(s)

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]

Affiliation

^[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

• Document type: Journal article
• Source: Tetrahedron; v. 70, n. 20, p. 3319-3326, MAY 20 2014.
• Web of Science Citations: 5

Abstract

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)

• FAPESP's process: 09/51602-5 - Chemical biology: new natural and synthetic molecular targets against cancer, structural studies, biological evaluation and mode of action
• Grantee: Ronaldo Aloise Pilli
• Support Opportunities: Research Projects - Thematic Grants
• FAPESP's process: 11/20033-5 - Synthesis of heterocycles using Morita-Baylis-Hillman adducts
• Grantee: Fernando Antonio Santos Coelho
• Support Opportunities: Regular Research Grants