Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne , EPFL-SB-ISIC-LSPN, BCH 5304, CH-1015 Lausanne, Switzerland.
J Am Chem Soc. 2013 Dec 26;135(51):19127-30. doi: 10.1021/ja4115192. Epub 2013 Dec 13.
A unified strategy allowing enantioselective total syntheses of (-)-mersicarpine, (-)-scholarisine G, (+)-melodinine E, (-)-leuconoxine, and (-)-leuconolam from a common cyclohexenone derivative was reported. The Suzuki-Miyaura reaction was used to couple two simple fragments incorporating the key elements for total synthesis, and unprecedented oxidation/reduction/cyclization processes were developed that converted the substituted cyclohexenone to either a mersicarpine or leuconoxine skeleton. In a reverse biomimetic synthesis fashion, (+)-melodinine E was converted to (-)-leuconolam under acidic conditions.
报道了一种统一的策略，可从一个共同的环己烯酮衍生物对 (-)- 乌头宁、(-)- 山豆根宁 G、(+) - 美罗定 E、(-)- 白屈菜红碱和 (-)- 白屈菜灵进行对映选择性全合成。Suzuki-Miyaura 反应用于偶联两个包含全合成关键要素的简单片段，开发了前所未有的氧化/还原/环化过程，可将取代的环己烯酮转化为乌头宁或白屈菜灵骨架。以反仿生合成的方式，在酸性条件下将 (+)- 美罗定 E 转化为 (-)- 白屈菜灵。
