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Concise Total Syntheses of the 6-7-5 Hamigeran Natural Products.

Baiyang JiangMingji Dai
Published in: Journal of the American Chemical Society (2023)
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).
Keyphrases
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  • electron transfer