香芹酮制备的 α-蒎烯衍生物的 C-C 键断裂作为复杂分子合成的一般策略,Accounts of Chemical Research

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香芹酮制备的 α-蒎烯衍生物的 C-C 键断裂作为复杂分子合成的一般策略
Accounts of Chemical Research ( IF 18.3 ) Pub Date : 2022-02-16 , DOI: 10.1021/acs.accounts.1c00783
Robert F Lusi ₁ , Melecio A Perea ₁ , Richmond Sarpong ₁

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复杂分子（例如，具有生物活性的次生代谢物）的制备仍然是化学合成的重要追求。凭借其复杂的结构，复杂的天然产物激发了全合成运动，从而导致构建分子的全新方式。在 20 世纪，出现了一种这样的范例，即使用天然存在的“手性池萜烯”作为全合成的起始材料。这些廉价且天然丰富的分子为天然产物的对映体特异性制备提供了一种易于获取的对映体富集材料来源。手性池萜最常见的应用是合成，其中它们的结构可以完全或大部分直接叠加到目标结构的一部分上。不太直接的用途，如果起始手性池萜的结构在目标结构中没有立即明显，则实施起来可能更具挑战性。然而，这些“非直观”的方法说明了基于手性池的策略的最终前景：任何单一的手性池萜烯都可以用于合成无限数量的结构多样的复杂合成目标。

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C–C Bond Cleavage of α-Pinene Derivatives Prepared from Carvone as a General Strategy for Complex Molecule Synthesis

The preparation of complex molecules (e.g., biologically active secondary metabolites) remains an important pursuit in chemical synthesis. By virtue of their sophisticated architectures, complex natural products inspire total synthesis campaigns that can lead to completely new ways of building molecules. In the twentieth century, one such paradigm which emerged was the use of naturally occurring “chiral pool terpenes” as starting materials for total synthesis. These inexpensive and naturally abundant molecules provide an easily accessed source of enantioenriched material for the enantiospecific preparation of natural products. The most common applications of chiral pool terpenes are in syntheses where their structure can, entirely or largely, be superimposed directly onto a portion of the target structure. Less straightforward uses, where the structure of the starting chiral pool terpene is not immediately evident in the structure of the target, can be more challenging to implement. Nevertheless, these “nonintuitive” approaches illustrate the ultimate promise of chiral pool-based strategies: that any single chiral pool terpene could be applied to syntheses of an indefinite number of structurally diverse complex synthetic targets.

更新日期：2022-02-16

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