The Asymmetric Total Synthesis Of Nature Product(-)-psychotriasine

3?-amino-pyrroloindoline skeleton are widely existed in various natural products and bioactive indole alkaloids,such as Psychotriasine.Psychotriasine as a representative and potential bioactive indole alkaloid was isolated from the leaves of Psychotria calocarpa in 2010.Since then,it attracted much attention from the organic synthetic and medicinal chemistry communities.As for the total synthesis of Psychotriasine,the key step is the enantioselective construction of 3?-amino-pyrroloindoline skeleton.Up to now,the general strategies for the synthesis of Psychotriasine are based on the dearomatization of tryptamines and its derivatives,while other strategies are rare reported.Focused on the total synthesis of Psychotriasine,our retrosynthetic analysis based on our previous work on the enantioselective Mannich reaction between readily available isatin-derived imines and aldehydes as raw materials and the Mannich reaction of aldehydes and ketones has been illustrated.After several attempts and failures,the asymmetric total synthesis of(-)-psychotriasine was achieved by a serial of process,such as LiAlH4-mediated reductive cyclization,Buchwald–Hartwig amination and Larock cyclization,etc.This work described herein can not only provide a new route for the total synthesis of natural product(-)-psychotriasine,but also serves as a new and efficient pathway for the construction of 3?-amino-pyrroloindoline skeleton.