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Concise Total Syntheses of the 6–7–5 Hamigeran Natural Products
[Image: see text] Herein, we report the total syntheses of four hamigeran natural products featuring a 6–7–5 tricyclic carbon skeleton. We utilized a palladium-catalyzed intramolecular cyclopropanol ring opening cross-coupling to build the central seven-membered ring and a series of oxidations inclu...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2023
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10472436/ https://www.ncbi.nlm.nih.gov/pubmed/37603855 http://dx.doi.org/10.1021/jacs.3c06031 |
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author | Jiang, Baiyang Dai, Mingji |
author_facet | Jiang, Baiyang Dai, Mingji |
author_sort | Jiang, Baiyang |
collection | PubMed |
description | [Image: see text] Herein, we report the total syntheses of four hamigeran natural products featuring a 6–7–5 tricyclic carbon skeleton. We utilized a palladium-catalyzed intramolecular cyclopropanol ring opening cross-coupling to build the central seven-membered ring and a series of oxidations including a challenging aromatic C–H oxidation to introduce the peripheral functionalities. This approach enabled us to achieve the first total syntheses of hamigeran C (14 steps), debromohamigeran I (12 steps), and hamigeran I (13 steps). Our synthesis also resulted in hamigeran G in 13 steps, which is significantly shorter than the previously reported one (24 steps, longest linear sequence). |
format | Online Article Text |
id | pubmed-10472436 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-104724362023-09-02 Concise Total Syntheses of the 6–7–5 Hamigeran Natural Products Jiang, Baiyang Dai, Mingji J Am Chem Soc [Image: see text] Herein, we report the total syntheses of four hamigeran natural products featuring a 6–7–5 tricyclic carbon skeleton. We utilized a palladium-catalyzed intramolecular cyclopropanol ring opening cross-coupling to build the central seven-membered ring and a series of oxidations including a challenging aromatic C–H oxidation to introduce the peripheral functionalities. This approach enabled us to achieve the first total syntheses of hamigeran C (14 steps), debromohamigeran I (12 steps), and hamigeran I (13 steps). Our synthesis also resulted in hamigeran G in 13 steps, which is significantly shorter than the previously reported one (24 steps, longest linear sequence). American Chemical Society 2023-08-21 /pmc/articles/PMC10472436/ /pubmed/37603855 http://dx.doi.org/10.1021/jacs.3c06031 Text en © 2023 The Authors. Published by 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 | Jiang, Baiyang Dai, Mingji Concise Total Syntheses of the 6–7–5 Hamigeran Natural Products |
title | Concise Total Syntheses
of the 6–7–5
Hamigeran Natural Products |
title_full | Concise Total Syntheses
of the 6–7–5
Hamigeran Natural Products |
title_fullStr | Concise Total Syntheses
of the 6–7–5
Hamigeran Natural Products |
title_full_unstemmed | Concise Total Syntheses
of the 6–7–5
Hamigeran Natural Products |
title_short | Concise Total Syntheses
of the 6–7–5
Hamigeran Natural Products |
title_sort | concise total syntheses
of the 6–7–5
hamigeran natural products |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10472436/ https://www.ncbi.nlm.nih.gov/pubmed/37603855 http://dx.doi.org/10.1021/jacs.3c06031 |
work_keys_str_mv | AT jiangbaiyang concisetotalsynthesesofthe675hamigerannaturalproducts AT daimingji concisetotalsynthesesofthe675hamigerannaturalproducts |