Cascade Cyclization, Dipolar Cycloaddition to Bridged Tricyclic Amines Related to the Daphniphyllum Alkaloids

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...

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Bibliographic Details
Published in:Organic letters 2011-03, Vol.13 (6), p.1267-1269
Main Authors: Coldham, Iain, Burrell, Adam J. M, Guerrand, Hélène D. S, Oram, Niall
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
Alkaloids - chemical synthesis
Alkaloids - chemistry
Amines - chemistry
Crystallography, X-Ray
Cyclization
Molecular Conformation
Molecular Structure
Saxifragaceae - chemistry
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol102961x