کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
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5273773 | 1385498 | 2009 | 5 صفحه PDF | دانلود رایگان |
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.
Two expedient approaches for the synthesis of spiro-oxindoles containing succinimide were investigated. From these results, the tandem halide displacement/amide coupling spiro-cyclization approach that extends our recent findings in this subject seems to be simple and effective. The spiro-cyclic systems obtained were then used to provide spiro-oxindoles containing γ-lactams and pyrroloisoquinolines by using reduction processes followed or not by π-cationic cyclization in acidic medium.Figure optionsDownload as PowerPoint slide
Journal: Tetrahedron Letters - Volume 50, Issue 31, 5 August 2009, Pages 4411–4415