4.4 Article

Concise, asymmetric total synthesis of spirotryprostatin A

Journal

TETRAHEDRON
Volume 60, Issue 42, Pages 9503-9515

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2004.07.047

Keywords

spirotryprostatin A; dipolar cycloaddition; azomethine ylide

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The structurally intriguing cell-cycle inhibitor spirotryprostatin A has been synthesized utilizing an azomethine ylide dipolar cycloaddition reaction as the key step. This pentacyclic alkaloid contains a prenylated tryptophan-derived oxindole moiety that has been created in a regiocontrolled and stereocontrolled manner in a single step. (C) 2004 Elsevier Ltd. All rights reserved.

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