Short Total Synthesis of (±)-Gelliusine E and 2,3'-Bis(indolyl)ethylamines via PTSA-Catalyzed Transindolylation

  • J Org Chem. 2021 Oct 1;86(19):13360-13370. doi: 10.1021/acs.joc.1c01461.
Chayamon Chantana  1 ,  Uthaiwan Sirion  1  2 ,  Panata Iawsipo  3  4 ,  Jaray Jaratjaroonphong  1  2
Affiliations
  • 1. Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Burapha University, Chonburi 20131, Thailand.
  • 2. Research Unit in Synthetic Compounds and Synthetic Analogues from Natural Product for Drug Discovery (RSND), Burapha University, Chonburi 20131, Thailand.
  • 3. Department of Biochemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Burapha University, Chonburi 20131, Thailand.
  • 4. Research Unit of Natural Bioactive Compounds for Healthcare Products Development, Burapha University, Chonburi 20131, Thailand.
PMID: 34528793 DOI: 10.1021/acs.joc.1c01461
Abstract

A first and short total synthesis of the marine Sponge 2,3'-bis(indolyl)ethylamine (2,3'-BIEA) alkaloid (±)-gelliusine E was performed in both a three-step divergent approach and a one-pot three-component approach with an overall yield of up to 58%. A key feature of the novel strategy is PTSA-catalyzed transindolylation of the readily synthesized 3,3'-BIEAs with tryptamine derivatives. The structure of the isolated natural product is revised as protonated (±)-gelliusine E (4'). By design, this modular route allows the rapid synthesis of Other members of the 2,3'-BIEA family, for example, (±)-6,6'-bis-(debromo)-gelliusine F and analogues with step economy, operational simplicity, and reduced waste. Furthermore, their cytotoxicity in breast Cancer cells was investigated.

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