通过复合同源二聚体交叉复分解反应合成阿扎唑类化合物的碳-碳片段。
Synthesis of the C-C fragment of the archazolids by complex -homodimer cross metathesis.
作者信息
Swick Steven M, Schaefer Sara L, O'Neil Gregory W
机构信息
Department of Chemistry, Western Washington University, Bellingham, WA, 98225, USA.
出版信息
Tetrahedron Lett. 2015 Jun 24;56(26):4039-4042. doi: 10.1016/j.tetlet.2015.05.014.
Abstract
A synthesis of the C-C fragment of the archazolids is described featuring a complex cross-metathesis coupling reaction between a -homodimer (prepared by silyl-tethered ring-closing metathesis) and the -terminal triene containing "eastern domain" of the archazolid natural products. This cross-metathesis was only successful when using the - as opposed to the monomer or -homodimer, with the -dimer added batchwise to minimize -isomerization. The product was obtained in an optimized 78% yield using the Hoveyda-Grubbs catalyst at 50 °C in toluene.
摘要
描述了阿奇唑类化合物C-C片段的合成，其特征在于α-同二聚体（通过硅烷基连接的闭环复分解反应制备）与阿奇唑类天然产物含“东部结构域”的β-末端三烯之间发生复杂的交叉复分解偶联反应。只有使用β-同二聚体（与单体或α-同二聚体相对）时，这种交叉复分解反应才成功，将β-二聚体分批加入以尽量减少β-异构化。使用霍维达-格鲁布斯催化剂，在50℃的甲苯中，以优化后的产率78%获得产物。
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