Total Synthesis of Thiostrepton, Part 1: Construction of the Dehydropiperidine/Thiazoline-Containing Macrocycle

A cornerstone of the RNA‐binding antibiotic thiostrepton, namely the dehydropiperidine–thiazoline macrocyclic domain (see formula), was constructed through a hetero‐Diels–Alder‐type dimerization of an azadiene and selective elaboration of the resulting dehydropiperidine system.

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Bibliographische Detailangaben
Veröffentlicht in:	Angewandte Chemie International Edition 2004-09, Vol.43 (38), p.5087-5092
Hauptverfasser:	Nicolaou, K. C., Safina, Brian S., Zak, Mark, Estrada, Anthony A., Lee, Sang Hyup
Format:	Artikel
Sprache:	eng
Schlagworte:	antibiotics azadienes cycloaddition Macrocyclic Compounds - chemical synthesis Molecular Conformation natural products Piperidines - chemical synthesis Piperidines - chemistry Thiazoles - chemical synthesis Thiazoles - chemistry Thiostrepton - chemical synthesis total synthesis
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Beschreibung
Zusammenfassung:	A cornerstone of the RNA‐binding antibiotic thiostrepton, namely the dehydropiperidine–thiazoline macrocyclic domain (see formula), was constructed through a hetero‐Diels–Alder‐type dimerization of an azadiene and selective elaboration of the resulting dehydropiperidine system.
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.200461340