Journal
ORGANIC LETTERS
Volume 13, Issue 6, Pages 1267-1269Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol102961x
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Funding
- EPSRC
- University of Sheffield
- Lilly UK
- EPSRC [EP/F06313X/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/F06313X/1] Funding Source: researchfish
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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.
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