Use of thiazoles in the halogen dance reaction: application to the total synthesis of WS75624 B.
Use of thiazoles in the halogen dance reaction: application to the total synthesis of WS75624 B.
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DOI：
10.1021/jo0351217
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发表时间：
2004-02
期刊：
影响因子：
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通讯作者：
Eric L. Stangeland;T. Sammakia
中科院分区：
文献类型：
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作者：
Eric L. Stangeland;T. Sammakia
本文报道了含吡啶-噻唑的天然产物WS 75624 B（1）的全合成。该合成通过适当官能化的吡啶和噻唑组分的Stille偶联进行，本文详细介绍了我们对使用卤素舞蹈反应制备所需噻唑的研究。描述了在噻唑上的各种卤素舞反应，包括新的一锅多步反应，其中在-78 ℃下在氯硅烷存在下用LDA处理2-溴噻唑并用亲电试剂淬灭，得到高度官能化的噻唑衍生物27。
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 degrees C and quenched with an electrophile to provide the highly functionalized thiazole derivatives 27.