Visible-Light-Induced Radical Cascade Cyclization: Synthesis of the ABCD Ring Cores of Camptothecins

J Org Chem. 2018 Mar 2;83(5):2840-2846. doi: 10.1021/acs.joc.7b03283. Epub 2018 Feb 12.

Abstract

A new strategy for constructing indolizino[1,2-b]quinolin-9(11H)-ones (ring cores of camptothecins) from readily available isocyanoarenes and N-(alkyl-2-yn-1-yl)pyridin-2(1H)-ones has been developed through a visible-light-induced radical cascade cyclization process. The reaction proceeds under mild conditions with fair to excellent yields. The easy introduction of substituents for both reactants and the broad functional group tolerance of the reaction make it a straightforward route to the cores of the marketed camptothecins and their derivatives.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Camptothecin / chemistry*
  • Catalysis
  • Chemistry Techniques, Synthetic
  • Cyclization
  • Light*
  • Photochemical Processes*
  • Quinolines / chemical synthesis*
  • Quinolines / chemistry

Substances

  • Quinolines
  • Camptothecin