Department of Chemistry, Ludwig-Maximilians-Universität München and Center of Integrated Protein Science , Butenandtstr. 5-13, 81377 Munich, Germany.
J Org Chem. 2013 Nov 1;78(21):10784-801. doi: 10.1021/jo401706r. Epub 2013 Oct 17.
The undecose nucleoside antibiotics herbicidin C and aureonuclemycin are biologically highly active and represent challenging targets for total synthesis. Herein, the gradual evolution of our synthetic strategy toward these natural products is described in detail. The initial route encompasses metalate addition chemistry but suffers from poor stereochemical control. In contrast, the ultimately successful strategy benefits from a variety of reagent-controlled stereoselective transformations, including a surprisingly facile and highly diastereoselective N-glycosylation process. The presented work also describes new building blocks that might find further application in carbohydrate chemistry.
未脱氧核苷抗生素草丁霉素 C 和金核霉素在生物学上具有高度的活性，是全合成的极具挑战性的目标。本文详细描述了我们针对这些天然产物的合成策略的逐步发展。最初的路线包括金属化物加成化学，但立体化学控制较差。相比之下，最终成功的策略得益于各种试剂控制的立体选择性转化，包括一个令人惊讶的简单和高度非对映选择性的 N-糖苷化过程。所呈现的工作还描述了可能在碳水化合物化学中进一步应用的新构建块。
