Formerly of the Clemens Schöpf Institut für Organische Chemie und Biochemie, Technische Universität Darmstadt, Darmstadt, Germany.
Adv Carbohydr Chem Biochem. 2020;77:121-149. doi: 10.1016/bs.accb.2020.05.001. Epub 2020 Jul 31.
This article presents a selection of topics from Professor Frieder W. Lichtenthaler's scientific lifework. It describes his contributions to, and further development of, the nitromethane cyclization of dialdehydes leading to amino sugars and amino nucleosides, as well as a new coupling methodology for purine nucleosides. A number of chiral building blocks derived from sugars like the "sugar enolones," enollactones, hydroxyhexenals, and their synthetic applications in natural product syntheses are covered. The article further describes the chemistry of "ulosyl bromides" and their glycosidation reactions, including those with bifunctional acceptors, which led to the synthesis of spectinomycin and gomphoside. Lichtenthaler's work on the preparation of synthetically useful building blocks from disaccharides that are readily available in bulk quantities, and his studies on the reactivity, as well as the selective O-functionalization of sucrose, higher oligosaccharides, and cyclodextrins based on computer simulations, are highlighted. The article also presents his research on the syntheses of chiral building blocks from readily available ketoses and their synthetic applications. Finally the chapter concludes with his significant contributions in the field of the history of carbohydrate chemistry.
本文从弗里德雷克·莱特恩塔勒教授的科学生涯中选取了一些主题。文中描述了他在糖醛缩合反应中引入硝基甲烷环化作用以合成氨基糖和氨基核苷方面的贡献，以及嘌呤核苷新的偶联方法。本文还介绍了一些手性砌块，如“糖烯酮”、烯内酯、羟基己烯醛及其在天然产物合成中的应用。文章进一步描述了“尿苷溴化物”及其糖苷化反应的化学性质，包括与双功能受体的糖苷化反应，这些反应导致了壮观霉素和gomphoside 的合成。莱特恩塔勒教授还研究了如何从大量易得的二糖制备具有合成用途的砌块，以及基于计算机模拟的蔗糖、高聚糖和环糊精的反应性和选择性 O-功能化。本文还介绍了他在利用易得的酮糖合成手性砌块及其应用方面的研究。最后，这一章节总结了他在碳水化合物化学历史领域的重要贡献。
