Total Synthesis of (±)–Exotine B

[Image: see text] The heterodimeric indole/coumarin natural product exotine B was synthesized for the first time. The carbon skeleton of the natural product was formed rapidly by a palladium-catalyzed Suzuki cross-coupling reaction and a gallium-catalyzed three-component [4 + 3] cycloaddition reacti...

Descripción completa

Detalles Bibliográficos
Autores principales: Cheng, Bichu, Volpin, Giulio, Morstein, Johannes, Trauner, Dirk
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2018
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6056846/
https://www.ncbi.nlm.nih.gov/pubmed/29978703
http://dx.doi.org/10.1021/acs.orglett.8b01817
_version_ 1783341410736406528
author Cheng, Bichu
Volpin, Giulio
Morstein, Johannes
Trauner, Dirk
author_facet Cheng, Bichu
Volpin, Giulio
Morstein, Johannes
Trauner, Dirk
author_sort Cheng, Bichu
collection PubMed
description [Image: see text] The heterodimeric indole/coumarin natural product exotine B was synthesized for the first time. The carbon skeleton of the natural product was formed rapidly by a palladium-catalyzed Suzuki cross-coupling reaction and a gallium-catalyzed three-component [4 + 3] cycloaddition reaction. An alternative biosynthesis of exotine B is proposed based on the total synthesis. Improved syntheses of coumarin natural products gleinadiene and coumurrayin are also reported.
format Online
Article
Text
id pubmed-6056846
institution National Center for Biotechnology Information
language English
publishDate 2018
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-60568462018-07-25 Total Synthesis of (±)–Exotine B Cheng, Bichu Volpin, Giulio Morstein, Johannes Trauner, Dirk Org Lett [Image: see text] The heterodimeric indole/coumarin natural product exotine B was synthesized for the first time. The carbon skeleton of the natural product was formed rapidly by a palladium-catalyzed Suzuki cross-coupling reaction and a gallium-catalyzed three-component [4 + 3] cycloaddition reaction. An alternative biosynthesis of exotine B is proposed based on the total synthesis. Improved syntheses of coumarin natural products gleinadiene and coumurrayin are also reported. American Chemical Society 2018-07-06 2018-07-20 /pmc/articles/PMC6056846/ /pubmed/29978703 http://dx.doi.org/10.1021/acs.orglett.8b01817 Text en Copyright © 2018 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Cheng, Bichu
Volpin, Giulio
Morstein, Johannes
Trauner, Dirk
Total Synthesis of (±)–Exotine B
title Total Synthesis of (±)–Exotine B
title_full Total Synthesis of (±)–Exotine B
title_fullStr Total Synthesis of (±)–Exotine B
title_full_unstemmed Total Synthesis of (±)–Exotine B
title_short Total Synthesis of (±)–Exotine B
title_sort total synthesis of (±)–exotine b
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6056846/
https://www.ncbi.nlm.nih.gov/pubmed/29978703
http://dx.doi.org/10.1021/acs.orglett.8b01817
work_keys_str_mv AT chengbichu totalsynthesisofexotineb
AT volpingiulio totalsynthesisofexotineb
AT morsteinjohannes totalsynthesisofexotineb
AT traunerdirk totalsynthesisofexotineb

Ejemplares similares