A diversity-oriented approach to indolocarbazoles via Fischer indolization and olefin metathesis: total synthesis of tjipanazole D and I

Org Biomol Chem. 2016 Oct 18;14(41):9868-9873. doi: 10.1039/c6ob01679k.

Abstract

New synthetic strategies to indolocarbazoles have been reported via two-fold Fischer indolization under green conditions using l-(+)-tartaric acid and N,N-dimethyl urea. Starting with cyclohexanone, a bench-top starting material, this methodology has been extended to the total synthesis of natural products such as tjipanazoles D and I as well as the core structure of asteropusazole and racemosin B. Here, atom economical reactions like ring-closing metathesis, enyne-metathesis, and the Diels-Alder reaction have been used as key steps. Diverse strategies demonstrated here are useful in medicinal chemistry and materials science to design a library of decorated indoles.

MeSH terms

  • Alkenes / chemistry*
  • Carbazoles / chemical synthesis*
  • Carbazoles / chemistry*
  • Chemistry Techniques, Synthetic
  • Indoles / chemistry*

Substances

  • Alkenes
  • Carbazoles
  • Indoles
  • tjipanazole D
  • tjipanazole I
  • carbazole