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Ring Rearrangement Metathesis in 7-Oxabicyclo[2.2.1]heptene (7-Oxanorbornene) Derivatives. Some Applications in Natural Product Chemistry.
Natural Product Communications ( IF 1.5 ) Pub Date : 2017-05-01
Silvia Roscales , Joaquín Plumet

Metathesis reactions is firmly established as a valuable synthetic tool in organic chemistry, clearly comparable with the venerable Diels-Alder and Wittig reactions and, more recently, with the metal-catalyzed cross-coupling reactions. Metathesis reactions can be considered as a fascinating synthetic methodology, allowing different variants regarding substrate (alkene and alkyne metathesis) and type of metathetical reactions. On the other hand, tandem metathesis reactions such.Ring Rearrangement Metathesis (RRM) and the coupling of metathesis reaction with other reactions of alkenes such as Diels-Alder or Heck reactions,.makes metathesis one of the most powerful and reliable synthetic procedure. In particular, Ring-Rearrangement Metathesis (RRM) refers to the combination of several metathesis transformations into a domino process such as ring- opening metathesis (ROM)/ring-closing metathesis (RCM) and ROM-cross metathesis (CM) in a one-pot operation. RRM delivers complex frameworks that are difficult to assemble by conventional methods constitutingan atom economic process. RRM is applicable to mono- and polycyclie systems of varying ring sizes such as cyclopropene, cyclobutene, cyclopentene, cyclohexene, pyran systems, bicyclo[2.2.1]heptene derivatives, bicyclo[2.2.2]octene derivatives, bicyclo[3.2.l]octene derivatives and bicyclo[3.2.1]octene derivatives. In this review our attention has focused on the RRM reactions in 7-oxabicyclo[2.2.I]heptene derivatives and on their application in the synthesis of natural products or significant subunits of them.

中文翻译:

7-氧杂双环[2.2.1]庚烯(7-氧杂降冰片烯)衍生物的环重排复分解。在天然产物化学中的一些应用。

易位反应已被牢固确立为有机化学中有价值的合成工具,可以与古老的Diels-Alder和Wittig反应,以及最近与金属催化的交叉偶联反应相媲美。复分解反应可以被认为是一种引人入胜的合成方法,允许有关底物(烯烃和炔复分解)和复分解反应类型的不同变化。另一方面,串联复分解反应,例如环重排复分解(RRM),以及复分解反应与烯烃的其他反应如迪尔斯-阿尔德反应或赫克反应的耦合,使复分解反应成为最有效和可靠的合成方法之一。特别是,环重排复分解(RRM)是指将多个复分解转换组合为一个多米诺过程,例如在一锅操作中进行开环复分解(ROM)/闭环复分解(RCM)和ROM交叉复分解(CM)。 。RRM提供了复杂的框架,这些框架很难通过构成原子经济过程的常规方法来组装。RRM适用于各种环大小的单环和多环系统,例如环丙烯,环丁烯,环戊烯,环己烯,吡喃体系,双环[2.2.1]庚烯衍生物,双环[2.2.2]辛烯衍生物,双环[3.2.l]辛烯衍生物和双环[3.2.1]辛烯衍生物。在这篇综述中,我们的注意力集中在7-氧杂双环[2.2.I]庚烯衍生物中的RRM反应及其在天然产物或其重要亚基的合成中的应用。
更新日期:2019-11-01
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