The (±)-6-Aza[1.0]triblattane Skeleton: Contraction beyond the Wilder–Culberson Ring System

Synthesis of the 6-aza[1.0]­triblattane skeleton and the unexpected construction of the 7-azatetracyclo­[4.2.1.02,5.03,7]­nonane framework are reported, as inspired by the Wilder–Culberson 1-aza[1.1]­triblattane ring system. The key steps to assess the 6-aza[1.0]­triblattane include accessing the 1,...

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Bibliographic Details
Published in:Organic letters 2022-01, Vol.24 (3), p.903-906
Main Authors: Fahrenhorst-Jones, Tyler, Bernhardt, Paul V, Savage, G. Paul, Williams, Craig M
Format: Article
Language:English
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Summary:Synthesis of the 6-aza[1.0]­triblattane skeleton and the unexpected construction of the 7-azatetracyclo­[4.2.1.02,5.03,7]­nonane framework are reported, as inspired by the Wilder–Culberson 1-aza[1.1]­triblattane ring system. The key steps to assess the 6-aza[1.0]­triblattane include accessing the 1,6-cycloaddition product from reaction of chlorosulfonyl isocyanate with cyclohept-1,3,5-triene followed by intramolecular electrocyclization and aminium radical cyclization.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c04240