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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 |
Sumario: | [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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