Oxidative Amidation of Phenols Through the Use of Hypervalent Iodine Reagents: Development and Applications
Oxidative Amidation of Phenols Through the Use of Hypervalent Iodine Reagents: Development and Applications
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DOI：
10.1002/chin.200814264
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发表时间：
2007-12
期刊：
影响因子：
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通讯作者：
M. Ciufolini;N. A. Braun;S. Canesi;M. Ousmer;J. J. Chang-J.;D. Chai
中科院分区：
文献类型：
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作者：
M. Ciufolini;N. A. Braun;S. Canesi;M. Ousmer;J. J. Chang-J.;D. Chai
这篇文章回顾了我们实验室设计的一系列反应，这些反应影响了苯酚氧化转化为4-氨基二烯酮。这种化学的一个显著特征是使用高价碘试剂，特别是二乙酰氧基碘苯（DIB），作为新转化背景下独特的氧化剂。这种方法的出现为生物碱合成创造了新的机会。我们在FR-901483、TAN-1251C、圆柱菌C和其他含氮天然产物方面的努力说明了该领域的一些应用。1介绍2背景3第一代酚类氧化酰胺化：恶唑啉途径4初步应用：FR-901483和TAN-1251C的全合成5第二代酚类氧化酰胺化：磺胺技术6应用：(-)-柱胞嘧啶C的全合成7第三代溶液：双分子反应8结论
This contribution reviews a family of reactions devised in our laboratory that effect the oxidative conversion of phenols into 4-amido-dienones. A salient feature of this chemistry is the use of hypervalent iodine reagents, especially diacetoxyiodobenzene (DIB), as uniquely capable oxidants in the context of the new transformation. The advent of this methodology has created new opportunities in alkaloid synthesis. Our efforts toward FR-901483, TAN-1251C, cylindricine C, and other nitrogenous natural products illustrate some applications in that domain. 1 Introduction 2 Background 3 First-Generation Oxidative Amidation of Phenols: The Oxazoline Route 4 Initial Applications: Total Synthesis of FR-901483 and of TAN-1251C 5 Second-Generation Oxidative Amidation of Phenols: Sulfonamide Technology 6 Applications: Total Synthesis of (-)-Cylindricine C 7 Third-Generation Solution: The Bimolecular Reaction 8 Conclusion