The Chemical Synthesis and Applications of Tropane Alkaloids

Alkaloids Chem Biol. 2019:81:151-233. doi: 10.1016/bs.alkal.2018.06.001. Epub 2018 Sep 7.

Abstract

Tropanes are an important class of alkaloid natural products that are found in plants all over the world. These compounds can exhibit significant biological activity and are among the oldest known medicines. In the early 19th century, tropanes were isolated, characterized, and synthesized by notable chemical researchers. Their significant biological activities have inspired tremendous research efforts toward their synthesis and the elucidation of their pharmacological activity both in academia and in industry. In this chapter, which addresses the developments in this field since 1994, the focus is on the synthesis of these compounds, and several examples of sophisticated synthetic protocols involving both asymmetric and catalytic approaches are described. In addition, the structures of more than 100 new alkaloids are included as well as the applications and pharmacological properties of some tropane alkaloids.

Keywords: Asymmetric synthesis; Biological activity; Catalysis; Cocaine; Total synthesis; Tropane alkaloids.

Publication types

  • Review

MeSH terms

  • Acylation
  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry
  • Alkaloids / pharmacology*
  • Alkylation
  • Catalysis
  • HIV / drug effects
  • HIV Infections / drug therapy
  • Humans
  • Ligands
  • Molecular Structure
  • Tropanes / chemical synthesis*
  • Tropanes / chemistry
  • Tropanes / pharmacology*

Substances

  • Alkaloids
  • Ligands
  • Tropanes