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Total Syntheses of Hosieines A-C.

ABSTRACT: The collective total syntheses of (±)-hosieines A-C with a cage-like tetracyclic framework have been realized, which includes the first syntheses of hosieines B-C. The key strategy of the synthesis employs a one-pot domino reaction that involves Cu-catalyzed [3+2] cycloaddition, 1,6-enone formation, and 1,6-aza-Michael addition forming the 5/6/6-aza-tricyclic skeleton. Other salient synthetic tactics comprise a challenging double bond migration and a 1,4-aza-Michael addition reaction to afford the tetracyclic framework.

SUBMITTER: Zhang J

PROVIDER: S-EPMC11005691 | biostudies-literature | 2024 Apr

REPOSITORIES: biostudies-literature

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Total Syntheses of Hosieines A-C.

Zhang Jiayang J Yan Xu X Zhang Qing-Bao QB Wang Fang F Yang Bin B Yang Yang Y

Advanced science (Weinheim, Baden-Wurttemberg, Germany) 20240207 14

The collective total syntheses of (±)-hosieines A-C with a cage-like tetracyclic framework have been realized, which includes the first syntheses of hosieines B-C. The key strategy of the synthesis employs a one-pot domino reaction that involves Cu-catalyzed [3+2] cycloaddition, 1,6-enone formation, and 1,6-aza-Michael addition forming the 5/6/6-aza-tricyclic skeleton. Other salient synthetic tactics comprise a challenging double bond migration and a 1,4-aza-Michael addition reaction to afford t ...[more]

PMID: 38326080

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