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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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Detalles Bibliográficos
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
Descripción
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).