Lebrun Stéphane, Couture Axel, Deniau Eric, Grandclaudon Pierre
Laboratoire de Chimie Organique Physique, associé à l'ENSCL, UMR 8009, Université des Sciences et Technologies de Lille 1, F-59655 Villeneuve d'Ascq, France.
Org Biomol Chem. 2003 May 21;1(10):1701-6. doi: 10.1039/b302168h.
A new and concise synthesis of enantiopure antipodes of alkaloid cherylline has been devised. The synthetic strategy relies upon the reduction of a diversely and polyprotected diarylenamine bearing a chiral auxiliary. Separation of diastereopure intermediates, concomitant deprotections and intramolecular reductive amination complete the synthesis of the natural (S)-enantiomer and of the unnatural (R)-configured antipode.
已设计出一种新的简洁合成方法来制备生物碱切里林的对映体纯对映异构体。该合成策略依赖于对带有手性助剂的多保护二芳基烯胺进行还原。分离非对映体纯中间体、同时进行脱保护和分子内还原胺化反应，完成了天然（S）-对映体和非天然（R）-构型对映体的合成。
