Firth James D, O'Brien Peter, Ferris Leigh
Department of Chemistry, University of York, Heslington, York YO10 5DD, UK.
Org Biomol Chem. 2014 Dec 14;12(46):9357-65. doi: 10.1039/c4ob01694g. Epub 2014 Oct 9.
The improved performance of the sparteine surrogate compared to sparteine in a range of applications has highlighted the need to develop an approach to the (-)-sparteine surrogate, previously inaccessible in gram-quantities. A multi-gram scale, chromatography-free synthesis of the racemic sparteine surrogate and its resolution via diastereomeric salt formation with (-)-O,O'-di-p-toluoyl-l-tartaric acid is reported. Resolution on a 10.0 mmol scale gave the diastereomeric salts in 33% yield from which (-)-sparteine surrogate of 93 : 7 er was generated. This work solves a key limitation: either enantiomer of the sparteine surrogate can now be readily accessed.
与鹰爪豆碱相比，鹰爪豆碱替代物在一系列应用中的性能有所改善，这突出表明需要开发一种方法来制备（-）-鹰爪豆碱替代物，此前无法获得克级量的该替代物。本文报道了一种多克规模、无需色谱法的外消旋鹰爪豆碱替代物的合成方法，以及通过与（-）-O，O'-二对甲苯酰基-L-酒石酸形成非对映体盐来拆分该替代物的方法。10.0 mmol规模的拆分以33%的产率得到非对映体盐，从中生成了对映体过量为93:7的（-）-鹰爪豆碱替代物。这项工作解决了一个关键限制：现在可以很容易地获得鹰爪豆碱替代物的任意一种对映体。
