Use of Thiazoles in the Halogen Dance Reaction: Application to the Total Synthesis of WS75624 B

The total synthesis of the pyridine−thiazole-containing natural product WS75624 B (1) is described. This synthesis proceeds via the Stille coupling of appropriately functionalized pyridine and thiazole components, and this paper details our studies on the use of the halogen dance reaction to prepare...

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Veröffentlicht in:	Journal of organic chemistry 2004-04, Vol.69 (7), p.2381-2385
Hauptverfasser:	Stangeland, Eric L, Sammakia, Tarek
Format:	Artikel
Sprache:	eng
Schlagworte:	Biological Factors - chemical synthesis Catalysis Chemistry Combinatorial Chemistry Techniques Exact sciences and technology Halogens - chemistry Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Indicators and Reagents Molecular Structure Organic chemistry Preparations and properties Pyridines - analysis Pyridines - chemical synthesis Thiazoles - analysis Thiazoles - chemical synthesis
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container_title	Journal of organic chemistry
container_volume	69
creator	Stangeland, Eric L Sammakia, Tarek
description	The total synthesis of the pyridine−thiazole-containing natural product WS75624 B (1) is described. This synthesis proceeds via the Stille coupling of appropriately functionalized pyridine and thiazole components, and this paper details our studies on the use of the halogen dance reaction to prepare the desired thiazole. Various halogen dance reactions on thizoles are described, including a novel one-pot multistep reaction in which 2-bromothiazole is treated with LDA in the presence of a silyl chloride at −78 °C and quenched with an electrophile to provide the highly functionalized thiazole derivatives 27.
doi_str_mv	10.1021/jo0351217
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Various halogen dance reactions on thizoles are described, including a novel one-pot multistep reaction in which 2-bromothiazole is treated with LDA in the presence of a silyl chloride at −78 °C and quenched with an electrophile to provide the highly functionalized thiazole derivatives 27.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>15049634</pmid><doi>10.1021/jo0351217</doi><tpages>5</tpages></addata></record>
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subjects	Biological Factors - chemical synthesis Catalysis Chemistry Combinatorial Chemistry Techniques Exact sciences and technology Halogens - chemistry Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Indicators and Reagents Molecular Structure Organic chemistry Preparations and properties Pyridines - analysis Pyridines - chemical synthesis Thiazoles - analysis Thiazoles - chemical synthesis
title	Use of Thiazoles in the Halogen Dance Reaction: Application to the Total Synthesis of WS75624 B
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