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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...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical
Society
2021
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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. |
format | Online Article Text |
id | pubmed-8509925 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | American Chemical
Society |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT hulingbowei totalsynthesisofthechlorinatedpentacyclicindolealkaloidambiguineg AT rawalvireshh totalsynthesisofthechlorinatedpentacyclicindolealkaloidambiguineg |