Institut für Chemie, Universität Potsdam, Karl-Liebknecht-Strasse 24-25, 14476, Potsdam-Golm, Germany.
Prog Chem Org Nat Prod. 2021;115:1-57. doi: 10.1007/978-3-030-64853-4_1.
Ten-membered lactones are commonly observed structures of natural products. They are mostly fungal metabolites, which often act as plant pathogens, but recently ten-membered lactones were identified as pheromones of frogs and termites. Although modern spectroscopic methods are nowadays routinely used to elucidate the structure of natural products, structural assignments of ten-membered lactones often remain incomplete or are surprisingly often erroneous. Most errors concern the absolute configuration. The examples discussed in this chapter demonstrate that enantioselective total synthesis is not only an efficient tool for corroborating or revising a proposed structure, but that the synthesis of different stereoisomers as references for gas chromatographic investigations can be a vital part of the structure elucidation process if only minute amounts of material are available. As a method of outstanding importance for the synthesis of ten-membered lactones olefin metathesis has emerged. Most of the examples discussed herein use one or more olefin metathesis reactions as key steps.
十员环内酯是天然产物中常见的结构。它们大多是真菌代谢物，通常作为植物病原体，但最近发现十员环内酯也是青蛙和白蚁的信息素。尽管现代光谱方法如今已常规用于阐明天然产物的结构，但十员环内酯的结构分配通常仍不完整，或者出人意料地经常出错。大多数错误涉及绝对构型。本章讨论的例子表明，对映选择性全合成不仅是证实或修正所提出结构的有效工具，而且如果仅获得微量材料，则作为气相色谱研究参考的不同立体异构体的合成可以成为结构阐明过程的重要组成部分。作为十员环内酯合成的一种非常重要的方法，烯烃复分解已经出现。本文讨论的大多数例子都将一个或多个烯烃复分解反应作为关键步骤。
