Journal
TETRAHEDRON LETTERS
Volume 50, Issue 31, Pages 4411-4415Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2009.02.114
Keywords
Pentacyclic spiro-oxindoles; 5,5-Spiroimides; Spirocyclization; N-Acyliminium species; Alkaloids
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Funding
- Syrian Government
- Pharmaceutical University of Damascus
- Slovak Grant Agency [1/0629/08]
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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 alpha-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. (C) 2009 Elsevier Ltd. All rights reserved.
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