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

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-cata...

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Veröffentlicht in:	Journal of organic chemistry 2021-10, Vol.86 (19), p.13360-13370
Hauptverfasser:	Chantana, Chayamon, Sirion, Uthaiwan, Iawsipo, Panata, Jaratjaroonphong, Jaray
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Sprache:	eng
Schlagworte:	Chemistry Chemistry, Organic Physical Sciences Science & Technology
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container_end_page	13370
container_issue	19
container_start_page	13360
container_title	Journal of organic chemistry
container_volume	86
creator	Chantana, Chayamon Sirion, Uthaiwan Iawsipo, Panata Jaratjaroonphong, Jaray
description	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.
doi_str_mv	10.1021/acs.joc.1c01461
format	Article
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title	Short Total Synthesis of (±)-Gelliusine E and 2,3′-Bis(indolyl)ethylamines via PTSA-Catalyzed Transindolylation
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