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Production and Synthetic Modifications of Shikimic Acid
Chemical Reviews ( IF 62.1 ) Pub Date : 2018-10-11 00:00:00 , DOI: 10.1021/acs.chemrev.8b00350
Nuno R. Candeias 1 , Benedicta Assoah 1 , Svilen P. Simeonov 2
Affiliation  

Shikimic acid is a natural product of industrial importance utilized as a precursor of the antiviral Tamiflu. It is nowadays produced in multihundred ton amounts from the extraction of star anise (Illicium verum) or by fermentation processes. Apart from the production of Tamiflu, shikimic acid has gathered particular notoriety as its useful carbon backbone and inherent chirality provide extensive use as a versatile chiral precursor in organic synthesis. This review provides an overview of the main synthetic and microbial methods for production of shikimic acid and highlights selected methods for isolation from available plant sources. Furthermore, we have attempted to demonstrate the synthetic utility of shikimic acid by covering the most important synthetic modifications and related applications, namely, synthesis of Tamiflu and derivatives, synthetic manipulations of the main functional groups, and its use as biorenewable material and in total synthesis. Given its rich chemistry and availability, shikimic acid is undoubtedly a promising platform molecule for further exploration. Therefore, in the end, we outline some challenges and promising future directions.

中文翻译:

Shi草酸的生产及合成改性

ki草酸是工业上重要的天然产物,被用作抗病毒达菲的前体。它是在从八角的提取multihundred吨量现今生产的(八角)或通过发酵过程。除了生产达菲以外,sh草酸还因其有用的碳骨架和固有的手性在有机合成中作为通用的手性前体而广泛使用,因此臭名昭著。这篇综述概述了of草酸生产的主要合成和微生物方法,并着重介绍了从可用植物来源中分离出来的精选方法。此外,我们试图通过涵盖最重要的合成修饰和相关应用来证明sh草酸的合成效用,这些合成和相关应用包括达菲及其衍生物的合成,主要官能团的合成操作以及其作为生物可再生材料的用途以及在总合成中的用途。 。鉴于其丰富的化学成分和可用性,iki草酸无疑是有希望进一步开发的平台分子。因此,最后,我们概述了一些挑战和有希望的未来方向。
更新日期:2018-10-11
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