Cascade cyclization, dipolar cycloaddition to bridged tricyclic amines related to the Daphniphyllum alkaloids
I Coldham, AJM Burrell, HDS Guerrand, N Oram
Index: Coldham, Iain; Burrell, Adam J. M.; Guerrand, Helene D. S.; Oram, Niall Organic Letters, 2011 , vol. 13, # 6 p. 1267 - 1269
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Citation Number: 43
Abstract
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 ...
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