Divergent total syntheses of lyconadins A and C

Angew Chem Int Ed Engl. 2014 Apr 7;53(15):3922-5. doi: 10.1002/anie.201400416. Epub 2014 Mar 5.

Abstract

Divergent and concise total syntheses of two lycopodium alkaloids, lyconadins A and C have been developed. The synthesis of lyconadin A, having potent neurotrophic activity, features an efficient one-pot ketal removal and formal aza-[4+2] cyclization to form the cagelike core structure. A tandem ketal removal/Mannich reaction was developed to build the tricyclic structure of lyconadin C. Both lyconadins A and C were synthesized from a pivotal intermediate.

Keywords: alkaloids; cyclizations; drug discovery; natural products; total synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biological Products / chemical synthesis*
  • Biological Products / chemistry
  • Cyclization
  • Drug Discovery
  • Molecular Structure
  • Polycyclic Compounds / chemical synthesis*
  • Polycyclic Compounds / chemistry
  • Stereoisomerism

Substances

  • Biological Products
  • Polycyclic Compounds
  • lyconadin C