Joshi Bhaskar D, Chisholm John D
Department of Chemistry, 1-014 Center for Science and Technology, Syracuse University, Syracuse, NY 13244.
Tetrahedron Lett. 2021 Aug 3;77. doi: 10.1016/j.tetlet.2021.153256. Epub 2021 Jul 1.
Pyrroloindolines and related systems are present in a large number of complex natural products. These core structures have generated considerable synthetic interest, as many of the compounds possess challenging, elaborate structures and interesting biological properties. Recently we have focused on using trichloroacetimidates for the synthesis of these fascinating molecules. Trichloroacetimidates can be used as an electrophilic source of an alkyl group to form the pyrroloindoline directly from tryptamine derivatives. In this manner trichloroacetimidates provide a flexible solution to forming highly functionalized pyrroloindoline core structures, needing only a catalytic amount of a Lewis acid to effect the requisite transformations.
吡咯并吲哚啉及其相关体系存在于大量复杂的天然产物中。这些核心结构引发了相当大的合成兴趣，因为许多此类化合物具有具有挑战性的精细结构和有趣的生物学特性。最近，我们专注于使用三氯乙酰亚胺酯来合成这些迷人的分子。三氯乙酰亚胺酯可作为烷基的亲电来源，直接从色胺衍生物形成吡咯并吲哚啉。通过这种方式，三氯乙酰亚胺酯为形成高度官能化的吡咯并吲哚啉核心结构提供了一种灵活的解决方案，只需要催化量的路易斯酸即可实现所需的转化。
