Total synthesis of the dictyodendrins as an arena to highlight emerging synthetic technologies

Nat Prod Rep. 2017 Aug 2;34(8):1010-1034. doi: 10.1039/c7np00018a.

Abstract

Covering: 1993-2017This review discusses the isolation, biological activity, and syntheses of the dictyodendrin class of natural products, covering the years 1993-2017. The dictyodendrins are a family of alkaloids isolated from marine sponges, Dictyodendrilla verongiformis and Ianthella sp., which possess a highly substituted pyrrolo[2,3-c]carbazole core at the phenol or quinone oxidation states. Dictyodendrins exhibit a wide range of biological activities, such as telomerase inhibition, BACE1 enzyme inhibition, and cytotoxicity against several cancer cell lines. The unique structure and interesting biological activities of dictyodendrins provided a platform for the application of novel synthetic methods including C-H insertion, C-H arylation, and electrocyclization cascades.

Publication types

  • Review
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids* / chemical synthesis
  • Alkaloids* / chemistry
  • Alkaloids* / isolation & purification
  • Alkaloids* / pharmacology
  • Animals
  • Biological Products* / chemical synthesis
  • Biological Products* / chemistry
  • Biological Products* / isolation & purification
  • Carbazoles / chemical synthesis*
  • Carbazoles / chemistry
  • Carbazoles / isolation & purification
  • Marine Biology
  • Molecular Structure
  • Porifera / chemistry*
  • Pyrroles / chemical synthesis*
  • Pyrroles / chemistry
  • Pyrroles / isolation & purification

Substances

  • Alkaloids
  • Biological Products
  • Carbazoles
  • Pyrroles
  • dictyodendrin A