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Skeletal diversification by C-C cleavage to access bicyclic frameworks from a common tricyclooctane intermediate.

ABSTRACT: Herein, the diversification of tricyclo[3.2.1.0^3,6]octane scaffolds to afford diverse bicyclic scaffolds is described. The strained tricyclooctanes are prepared in two steps featuring a blue light-mediated [2+2] cycloaddition. Strategies for the cleavage of this scaffold were then explored resulting in the selective syntheses of the bicyclo[3.1.1]heptane, bicyclo[3.2.1]octane, and bicyclo[3.2.0]heptane cores. These findings may guide future studies of C-C cleavage reactions in strained carbon frameworks and their application in complex molecule synthesis.

SUBMITTER: Bakanas I

PROVIDER: S-EPMC10518267 | biostudies-literature | 2023 Mar

REPOSITORIES: biostudies-literature

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Skeletal diversification by C-C cleavage to access bicyclic frameworks from a common tricyclooctane intermediate.

Bakanas Ian I Tang Jess C JC Sarpong Richmond R

Chemical communications (Cambridge, England) 20230328 26

Herein, the diversification of tricyclo[3.2.1.03,6]octane scaffolds to afford diverse bicyclic scaffolds is described. The strained tricyclooctanes are prepared in two steps featuring a blue light-mediated [2+2] cycloaddition. Strategies for the cleavage of this scaffold were then explored resulting in the selective syntheses of the bicyclo[3.1.1]heptane, bicyclo[3.2.1]octane, and bicyclo[3.2.0]heptane cores. These findings may guide future studies of C-C cleavage reactions in straine ...[more]

PMID: 36916206

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