Department of Chemistry , Tufts University , 62 Talbot Avenue , Medford , Massachusetts 02155 , United States.
School of Chemistry , University of Bristol , Cantock's Close , Bristol BS8 1TS , United Kingdom.
Chem Rev. 2018 Sep 12;118(17):7931-7985. doi: 10.1021/acs.chemrev.7b00731. Epub 2018 Jun 28.
Deoxy-sugars often play a critical role in modulating the potency of many bioactive natural products. Accordingly, there has been sustained interest in methods for their synthesis over the past several decades. The focus of much of this work has been on developing new glycosylation reactions that permit the mild and selective construction of deoxyglycosides. This Review covers classical approaches to deoxyglycoside synthesis, as well as more recently developed chemistry that aims to control the selectivity of the reaction through rational design of the promoter. Where relevant, the application of this chemistry to natural product synthesis will also be described.
脱氧糖在调节许多生物活性天然产物的活性方面常常起着关键作用。因此,在过去几十年中,人们一直致力于开发它们的合成方法。这项工作的重点主要集中在开发新的糖苷化反应上,这些反应可以温和、选择性地构建脱氧糖苷。这篇综述涵盖了脱氧糖苷合成的经典方法,以及最近开发的旨在通过合理设计促进剂来控制反应选择性的化学方法。在相关情况下,还将描述这种化学方法在天然产物合成中的应用。