Synthetic studies on discorhabdin V: Construction of the A–F hexacyclic framework

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Abstract

This paper describes synthetic studies on a discorhabdin alkaloid with C2-N18 bond comprising the A–F hexa-cyclic framework. This specific bond was formed at the early stage of the synthesis by Mitsunobu reaction, and then a tryptamine derivative with E ring was converted to a tricyclic o-quinone intermediate via an aerobic oxidative cascade cyclization. Later in the synthesis, the D/E/F ring system incorporating E/D aza-spirocycle with C6 quaternary carbon center and the F/E aza-bicyclo[3.3.1]nonane systems were constructed via an intramolecular Heck cyclization of the halogenated tricyclic o-quinone.

Original languageEnglish
Article number153333
JournalTetrahedron Letters
Volume81
DOIs
Publication statusPublished - 2021 Sep 28

Keywords

  • Alkaloids
  • Disocrhabdin
  • Pyrroloiminoquinone

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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