25172-04-7Relevant academic research and scientific papers
Cascade cyclization, dipolar cycloaddition to bridged tricyclic amines related to the daphniphyllum alkaloids
Coldham, Iain,Burrell, Adam J. M.,Guerrand, Helene D. S.,Oram, Niall
, p. 1267 - 1269 (2011)
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.
