Dpto. de Química Orgánica, Facultad de Ciencias Químicas, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008 Salamanca, Spain.
Molecules. 2020 Mar 13;25(6):1308. doi: 10.3390/molecules25061308.
The asymmetric synthesis of a compound with the cyclopentan[c]pyran core of iridoid natural products in four steps and 40% overall yield is reported. Our methodology includes a one-pot tandem domino reaction which provides a trisubstituted cyclopentane with five new completely determined stereocenters, which were determined through 2D homo and heteronuclear NMR and n.O.e. experiments on different compounds specially designed for this purpose, such as a dioxane obtained from a diol. Due to their pharmaceutical properties, including sedative, analgesic, anti-inflammatory, CNS depressor or anti-conceptive effects, this methodology to produce the abovementioned iridoid derivatives, is an interesting strategy in terms of new drug discovery as well as pharmaceutical development.
报道了以 40%的总收率，经四步反应从具有环戊[c]吡喃核心的环烯醚萜天然产物中不对称合成该化合物。我们的方法包括一锅串联多步反应，提供了一个带有五个新的完全确定的立体中心的三取代环戊烷，这些立体中心是通过二维同核和异核 NMR 以及专门为此目的设计的不同化合物的 n.O.e.实验确定的，例如从二醇得到的二氧六环。由于这些化合物具有镇静、镇痛、抗炎、CNS 抑制剂或避孕作用等药物特性，因此，这种方法来制备上述环烯醚萜衍生物，无论是在新药发现还是药物开发方面，都是一种很有前途的策略。
