Total synthesis of (±)-decursivine via BINOL-phosphoric acid catalyzed tandem oxidative cyclization

The synthesis of tetracyclic indole alkaloid (±)-decursivine was accomplished using BINOL-phosphoric acid catalyzed tandem oxidative cyclization as a key step with (bis(trifluoroacetoxy)iodo)benzene (PIFA) as an oxidizing agent. This represents one of the shortest and highest yielding routes for the...

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Autores principales: Parvatkar, Prakash T., Smotkin, Eugene S., Manetsch, Roman
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2021
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8497573/
https://www.ncbi.nlm.nih.gov/pubmed/34620892
http://dx.doi.org/10.1038/s41598-021-99064-8
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author Parvatkar, Prakash T.
Smotkin, Eugene S.
Manetsch, Roman
author_facet Parvatkar, Prakash T.
Smotkin, Eugene S.
Manetsch, Roman
author_sort Parvatkar, Prakash T.
collection PubMed
description The synthesis of tetracyclic indole alkaloid (±)-decursivine was accomplished using BINOL-phosphoric acid catalyzed tandem oxidative cyclization as a key step with (bis(trifluoroacetoxy)iodo)benzene (PIFA) as an oxidizing agent. This represents one of the shortest and highest yielding routes for the synthesis of (±)-decursivine from readily available starting materials.
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spelling pubmed-84975732021-10-12 Total synthesis of (±)-decursivine via BINOL-phosphoric acid catalyzed tandem oxidative cyclization Parvatkar, Prakash T. Smotkin, Eugene S. Manetsch, Roman Sci Rep Article The synthesis of tetracyclic indole alkaloid (±)-decursivine was accomplished using BINOL-phosphoric acid catalyzed tandem oxidative cyclization as a key step with (bis(trifluoroacetoxy)iodo)benzene (PIFA) as an oxidizing agent. This represents one of the shortest and highest yielding routes for the synthesis of (±)-decursivine from readily available starting materials. Nature Publishing Group UK 2021-10-07 /pmc/articles/PMC8497573/ /pubmed/34620892 http://dx.doi.org/10.1038/s41598-021-99064-8 Text en © The Author(s) 2021 https://creativecommons.org/licenses/by/4.0/Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) .
spellingShingle Article
Parvatkar, Prakash T.
Smotkin, Eugene S.
Manetsch, Roman
Total synthesis of (±)-decursivine via BINOL-phosphoric acid catalyzed tandem oxidative cyclization
title Total synthesis of (±)-decursivine via BINOL-phosphoric acid catalyzed tandem oxidative cyclization
title_full Total synthesis of (±)-decursivine via BINOL-phosphoric acid catalyzed tandem oxidative cyclization
title_fullStr Total synthesis of (±)-decursivine via BINOL-phosphoric acid catalyzed tandem oxidative cyclization
title_full_unstemmed Total synthesis of (±)-decursivine via BINOL-phosphoric acid catalyzed tandem oxidative cyclization
title_short Total synthesis of (±)-decursivine via BINOL-phosphoric acid catalyzed tandem oxidative cyclization
title_sort total synthesis of (±)-decursivine via binol-phosphoric acid catalyzed tandem oxidative cyclization
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8497573/
https://www.ncbi.nlm.nih.gov/pubmed/34620892
http://dx.doi.org/10.1038/s41598-021-99064-8
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