Affiliation:
1. Departamento de Química Orgánica, Instituto Universitario de Bio-Orgánica Antonio González (SINTESTER), Universidad de La Laguna, Avda. Astrofísico Fco. Sánchez 2, 38206 La Laguna, Spain
Abstract
The 5,8-disubstituted indolizidines are the largest family of indolizidines isolated from the skin of amphibians. These compounds exhibit interesting biological activities such as noncompetitive blockers of nicotinic receptors. In this paper, we present a short, simple, and general synthesis of these alkaloids based on the hetero Diels–Alder reaction between suitable monoactivated dienes and Δ1-pyrroline as the dienophile. The selectivity of the process is explained based on computational studies. Concise synthesis of the indolizidine alkaloid 181B from a hetero Diels–Alder reaction was accomplished in four steps.
Subject
Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science
Reference40 articles.
1. Indolizidine and quinolizidine alkaloids;Michael;Nat. Prod. Rep.,2008
2. Chapter One-Simple Indolizidine and Quinolizidine Alkaloids;The Alkaloids: Chemistry and Biology,2016
3. De Rop, A.-S., Rombaut, J., Willems, T., De Graeve, M., Vanhaecke, L., Hulpiau, P., De Maeseneire, S.L., De Mol, M.L., and Soetaert, W.K. (2022). Novel Alkaloids from Marine Actinobacteria: Discovery and Characterization. Mar. Drugs, 20.
4. Biologically active indolizidine alkaloids;Zhang;Med. Res. Rev.,2021
5. Indolizidine Alkaloids: Prospective Lead Molecules in Medicinal Chemistry;Sharma;Curr. Tradit. Med.,2021