Concise, Asymmetric Total Synthesis of Spirotryprostatin A

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 st...

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Veröffentlicht in:	Organic letters 2003-08, Vol.5 (17), p.3135-3137
Hauptverfasser:	Onishi, Tomoyuki, Sebahar, Paul R, Williams, Robert M
Format:	Artikel
Sprache:	eng
Schlagworte:	Azo Compounds - chemistry Cyclization Indole Alkaloids - chemical synthesis Piperazines - chemical synthesis Piperazines - chemistry Spiro Compounds - chemical synthesis Stereoisomerism Tryptophan - analogs & derivatives
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Beschreibung
Zusammenfassung:	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.
ISSN:	1523-7060 1523-7052
DOI:	10.1021/ol0351910