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

ABSTRACT: 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).

SUBMITTER: Jiang B

PROVIDER: S-EPMC10472436 | biostudies-literature | 2023 Aug

REPOSITORIES: biostudies-literature

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

Jiang Baiyang B Dai Mingji M

Journal of the American Chemical Society 20230821 34

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 hamiger ...[more]

PMID: 37603855

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