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Total Synthesis of the Chlorinated Pentacyclic Indole Alkaloid (+)-Ambiguine G

[Image: see text] Reported herein is the total synthesis of (+)-ambiguine G, the first member of the chlorinated pentacyclic ambiguines to yield to chemical synthesis. The synthesis is accomplished through a convergent strategy that proceeds in 10 steps from (S)-carvone oxide. Pivotal to the concise...

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Autores principales: Hu, Lingbowei, Rawal, Viresh H.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8509925/
https://www.ncbi.nlm.nih.gov/pubmed/34279940
http://dx.doi.org/10.1021/jacs.1c05762
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author Hu, Lingbowei
Rawal, Viresh H.
author_facet Hu, Lingbowei
Rawal, Viresh H.
author_sort Hu, Lingbowei
collection PubMed
description [Image: see text] Reported herein is the total synthesis of (+)-ambiguine G, the first member of the chlorinated pentacyclic ambiguines to yield to chemical synthesis. The synthesis is accomplished through a convergent strategy that proceeds in 10 steps from (S)-carvone oxide. Pivotal to the concise route is the successful realization of a [4+3] cycloaddition that conjoins two easily synthesized components of the carbon framework of the natural product. Also featured in the synthesis is the efficient, diastereoselective construction of a key vinylated chloro ketone and the unprecedented, one-pot reduction–elimination–oxidation sequence that transforms an enone to an advanced hydroxylated-diene intermediate.
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spelling pubmed-85099252021-10-13 Total Synthesis of the Chlorinated Pentacyclic Indole Alkaloid (+)-Ambiguine G Hu, Lingbowei Rawal, Viresh H. J Am Chem Soc [Image: see text] Reported herein is the total synthesis of (+)-ambiguine G, the first member of the chlorinated pentacyclic ambiguines to yield to chemical synthesis. The synthesis is accomplished through a convergent strategy that proceeds in 10 steps from (S)-carvone oxide. Pivotal to the concise route is the successful realization of a [4+3] cycloaddition that conjoins two easily synthesized components of the carbon framework of the natural product. Also featured in the synthesis is the efficient, diastereoselective construction of a key vinylated chloro ketone and the unprecedented, one-pot reduction–elimination–oxidation sequence that transforms an enone to an advanced hydroxylated-diene intermediate. American Chemical Society 2021-07-19 2021-07-28 /pmc/articles/PMC8509925/ /pubmed/34279940 http://dx.doi.org/10.1021/jacs.1c05762 Text en © 2021 American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Hu, Lingbowei
Rawal, Viresh H.
Total Synthesis of the Chlorinated Pentacyclic Indole Alkaloid (+)-Ambiguine G
title Total Synthesis of the Chlorinated Pentacyclic Indole Alkaloid (+)-Ambiguine G
title_full Total Synthesis of the Chlorinated Pentacyclic Indole Alkaloid (+)-Ambiguine G
title_fullStr Total Synthesis of the Chlorinated Pentacyclic Indole Alkaloid (+)-Ambiguine G
title_full_unstemmed Total Synthesis of the Chlorinated Pentacyclic Indole Alkaloid (+)-Ambiguine G
title_short Total Synthesis of the Chlorinated Pentacyclic Indole Alkaloid (+)-Ambiguine G
title_sort total synthesis of the chlorinated pentacyclic indole alkaloid (+)-ambiguine g
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8509925/
https://www.ncbi.nlm.nih.gov/pubmed/34279940
http://dx.doi.org/10.1021/jacs.1c05762
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