Sennari Goh, Yamagishi Hiroki, Sarpong Richmond
Department of Chemistry, University of California, Berkeley, CA 94720, United States.
Ōmura Satoshi Memorial Institute and Graduate School of Infection Control Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan.
Chem Lett. 2024 Oct 30;53(11):upae204. doi: 10.1093/chemle/upae204. eCollection 2024 Nov.
Camphor and related monoterpenoid natural products have served as versatile "chiral pool" materials in organic chemistry for over half a century. Historically, many researchers have used a variety of transformations involving orchestrated rearrangements of the bornane skeleton to functionalize the camphor framework, expanding the utility of this chiral building block. Recent developments in C-H functionalization methodologies provide myriad opportunities to derivatize the camphor framework in a selective and predictable fashion. In this review, a short summary of the methods for functionalization of the camphor scaffold using rearrangement chemistry is provided followed by a discussion of emerging methods for directed C-H functionalizations that provide diverse new ways to derivatize the camphor framework.
半个多世纪以来，樟脑及相关单萜类天然产物在有机化学中一直作为通用的“手性池”材料。从历史上看，许多研究人员利用了各种涉及莰烷骨架精心重排的转化反应来使樟脑骨架功能化，从而扩展了这种手性构建单元的用途。C-H官能化方法的最新进展为以选择性和可预测的方式衍生樟脑骨架提供了无数机会。在这篇综述中，首先简要总结了使用重排化学对樟脑支架进行功能化的方法，随后讨论了新兴的定向C-H官能化方法，这些方法为衍生樟脑骨架提供了多种新途径。
