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Toward the improvement of the tandem halide displacement/amide coupling spiro-cyclization as a new route to γ-lactam and pyrroloisoquinoline templates

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
50
Issue
31
Identifiers
DOI: 10.1016/j.tetlet.2009.02.114
Keywords
  • Pentacyclic Spiro-Oxindoles
  • 5
  • 5-Spiroimides
  • Spirocyclization
  • N-Acyliminium Species
  • Alkaloids

Abstract

Abstract Two efficient and rapid accesses to spiro-oxindole entities bearing an imide function were presented, and their performance was compared. The key components are N-substituted α-bromoacetamides to reach these derivatives in tandem process. The resulting spiro-imides from these methodologies were regioselectively reduced into corresponding N-acyliminium precursors, which were subsequently submitted to an intramolecular cyclization to provide pentacyclic spiro-oxindole architecture analogues to pteropodine and spirotryprostatin-B alkaloids with high diastereoselective control.

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