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Org Lett. 2011 Mar 18;13(6):1267-9. doi: 10.1021/ol102961x. Epub 2011 Feb 11.

Cascade cyclization, dipolar cycloaddition to bridged tricyclic amines related to the Daphniphyllum alkaloids.

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Department of Chemistry, University of Sheffield, Brook Hill, Sheffield, S3 7HF, UK.


A tandem one-pot reaction of an aldehyde with a primary amine involving condensation and then cyclization (N-alkylation), followed by intramolecular dipolar cycloaddition of the resulting nitrone or azomethine ylide, provides a synthesis of bridged tricyclic amines. The reaction was most successful using hydroxylamine, and when the dipolarophile was an unsaturated ester, subsequent reduction of the N-O bond and cyclization to the lactam provided the core ring system of the yuzurimine, daphnilactone B, and bukittinggine type Daphniphyllum alkaloids.

[Indexed for MEDLINE]

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