Aza-analogues of podophyllotoxin were synthesized in two steps from N-substituted tetronamides. The acid-mediated benzhydrylation of N-substituted tetronamides with a suitably functionalized benzhydrol quantitatively afforded the cyclization precursors. The target pentacyclic 4-aza-2,3-didehydropodo-phyllotoxins were next obtained via an intramolecular copper-mediated Ullmann-type N-arylation.
N-alkyl Tetronamides as Ambident Nucleophilic building blocks for the Synthesis of new 4-Aza-2,3-didehydropodophyllotoxins
2008
Abstract
Aza-analogues of podophyllotoxin were synthesized in two steps from N-substituted tetronamides. The acid-mediated benzhydrylation of N-substituted tetronamides with a suitably functionalized benzhydrol quantitatively afforded the cyclization precursors. The target pentacyclic 4-aza-2,3-didehydropodo-phyllotoxins were next obtained via an intramolecular copper-mediated Ullmann-type N-arylation.File in questo prodotto:
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