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Synthetic efforts toward the bicyclo[3.2.1]octane fragment of rhodojaponin III.

ABSTRACT: Rhodojaponin III is a grayanane-type diterpenoid natural product with a novel chemical scaffold. It shows potent antinociceptive activity and may represent a new class of natural non-opioid analgesics with a novel mode of action. We explored the Au(I)-catalyzed Conia-ene cyclization and the Mn(III)-mediated radical cyclization of alkynyl ketones for the synthesis of the bicyclo[3.2.1]octane fragment of rhodojaponin III. These strategies will be applicable in the synthesis of rhodojaponin III and analogs for future biological studies.

SUBMITTER: Webster CG

PROVIDER: S-EPMC8153367 | biostudies-literature | 2021 May

REPOSITORIES: biostudies-literature

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Synthetic efforts toward the bicyclo[3.2.1]octane fragment of rhodojaponin III.

Webster Caroline G CG Park Hyeri H Ennis Amanda F AF Hong Jiyong J

Tetrahedron letters 20210406

Rhodojaponin III is a grayanane-type diterpenoid natural product with a novel chemical scaffold. It shows potent antinociceptive activity and may represent a new class of natural non-opioid analgesics with a novel mode of action. We explored the Au(I)-catalyzed Conia-ene cyclization and the Mn(III)-mediated radical cyclization of alkynyl ketones for the synthesis of the bicyclo[3.2.1]octane fragment of rhodojaponin III. These strategies will be applicable in the synthesis of rhodojaponin III and ...[more]

PMID: 34054153

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