Local Desymmetrization through Diastereotopic Group Selection: An Enabling Strategy for Natural Product Synthesis.
Local Desymmetrization through Diastereotopic Group Selection: An Enabling Strategy for Natural Product Synthesis.
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DOI：
10.1002/ejoc.201601481
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发表时间：
2017-03-17
影响因子：
2.8
通讯作者：
Johnson JS
中科院分区：
文献类型：
--
作者：
Horwitz MA;Johnson JS
去对称化策略在化学合成中的应用已经实现了从根本上新的合成序列，从而有效地创建了密集和多功能的立体化学阵列。对位群体歧视已经成为一种成熟的全球去对称化方法，而概念上独特的非对位群体歧视局部去对称化策略有其自身的优势。本文重点介绍了局部去对称化在天然产物合成中的应用，并特别强调了非对映异位基团歧视所产生的效率。局部去对称化被细分为三种不同的流形；每种范式下的例子都被列出并进行了比较。综述了天然产物合成中三种不同的非对映异位基团选择模式。重点介绍了能够利用局部去对称化快速建立立体化学复杂性的案例研究。
The application of desymmetrization strategies in chemical synthesis has allowed fundamentally new synthetic sequences that efficiently create dense and polyfunctional stereochemical arrays. Enantiotopic group discrimination has become a well-established method of global desymmetrization, while the conceptually unique strategy of local desymmetrization by diastereotopic group discrimination has its own advantages. This microreview focuses on the application of local desymmetrization in natural product synthesis and places a particular emphasis on the efficiency engendered by diastereotopic group discrimination. Local desymmetrization is subdivided into three distinct manifolds; examples under each paradigm are presented and compared. Three distinct modes of diastereotopic group selection in natural product synthesis are reviewed. Case studies that enable the rapid buildup of stereochemical complexity using local desymmetrization are emphasized.