[4 + 2] Cyclization or Lossen Rearrangement: Rhodium-Catalyzed Divergent Synthesis of Carboline Derivatives with Anticancer Activity

Org Lett. 2024 May 24;26(20):4212-4217. doi: 10.1021/acs.orglett.4c01050. Epub 2024 May 14.

Abstract

An unusual rhodium-catalyzed C-H activation/Lossen rearrangement/oxa-Michael addition tandem cyclization has been achieved along with a tunable well-known C-H activation/[4 + 2] annulation, leading to regio-, chemo-, and diastereoselective access to diverse pentacyclic α-carbolines and β-carboline-1-one derivatives in moderate to good yields with significant anticancer activity.

MeSH terms

  • Antineoplastic Agents* / chemical synthesis
  • Antineoplastic Agents* / chemistry
  • Antineoplastic Agents* / pharmacology
  • Carbolines* / chemical synthesis
  • Carbolines* / chemistry
  • Carbolines* / pharmacology
  • Catalysis
  • Cyclization
  • Drug Screening Assays, Antitumor
  • Humans
  • Molecular Structure
  • Rhodium* / chemistry
  • Stereoisomerism

Substances

  • Rhodium
  • Carbolines
  • Antineoplastic Agents