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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...

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Autores principales: Jiang, Baiyang, Dai, Mingji
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
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).
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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
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