Indole-based alkaloids are well-known in the literature for their diverse biological properties. Polysubstituted optically active tetrahydro-β-carboline derivatives functionalized on C-1 position are the common structural motif in most of the indole-based alkaloids, as well as highly marketed drugs. The stereoselective Pictet-Spengler reaction is one of the currently most important synthetic techniques used for the preparation of these privileged tetrahydro-β-carboline scaffolds. To date, there are numerous research reports that have been published on the synthesis of the tetrahydro-β-carboline scaffold both on solid phase, as well as in solution phase. Moreover rapid growth has been observed for the enantioselective synthesis of tetrahydro-β-carboline scaffold using chiral organocatalysts. In this Review, efforts have been taken to shed light on the latest information available on different strategies to synthesize tetrahydro-β-carboline both on solid phase and in solution phase during the last 20 years. Furthermore, we believe that the present synthetic methodologies covered in this Review will help to improve the status of this privileged tetrahydro-β-carboline scaffold in its use for drug discovery.

中文翻译：

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Pictet-Spengler反应在含四氢-β-咔啉骨架的吲哚类生物碱的组合化学中的应用。

基于吲哚的生物碱因其多样的生物学特性而在文献中广为人知。在大多数基于吲哚的生物碱以及市售药物中，在C-1位置官能化的多取代光学活性四氢-β-咔啉衍生物是常见的结构基序。立体选择性Pictet-Spengler反应是目前用于制备这些特有的四氢-β-咔啉骨架的最重要的合成技术之一。迄今为止，已经发表了许多关于在固相和溶液相上合成四氢-β-咔啉支架的研究报告。此外，已经观察到使用手性有机催化剂对四氢-β-咔啉支架的对映选择性合成的快速增长。在这篇评论中，在过去的20年中，我们努力揭示了有关固相和溶液相合成四氢-β-咔啉的不同策略的最新信息。此外，我们认为，本综述中涵盖的当前合成方法学将有助于改善这种特权的四氢-β-咔啉支架在药物开发中的使用状况。