Lahm Günther, Deichmann Jan-Gernot, Rauen Anna Lisa, Opatz Till
Institute of Organic Chemistry, University of Mainz , Duesbergweg 10-14, D-55128 Mainz, Germany.
J Org Chem. 2015 Feb 6;80(3):2010-6. doi: 10.1021/jo502842s. Epub 2015 Jan 27.
A facile one-pot synthesis of protoberberines from readily accessible 1,2,3,4-tetrahydroisoquinoline-1-carbonitriles and 1,2-bis(bromomethyl)arenes is described. The reaction cascade comprises four consecutive transformations, all of which can be effected under a single set of conditions. Ten protoberberines, including the alkaloids pseudopalmatine and pseudoepiberberine, were prepared in yields up to 86% according to this strategy. No chromatographic purification of the products is required, and the route is devoid of any protecting group manipulations.
描述了一种从易于获得的1,2,3,4-四氢异喹啉-1-甲腈和1,2-双（溴甲基）芳烃简便一锅法合成原小檗碱的方法。该反应串联包括四个连续的转化步骤，所有这些步骤都可以在一组条件下进行。根据该策略，制备了十种原小檗碱，包括生物碱假掌叶防己碱和假表小檗碱，产率高达86%。产物无需色谱纯化，且该路线无需任何保护基操作。
