Synthetic studies toward strictamine of natural products via an indolenine as a key intermediate

2017 Fiscal Year Final Research Report

• Project/Area Number: 26870101
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Synthetic chemistry; Chemical pharmacy
• Research Institution: Chiba University
• Principal Investigator: Kagawa Natsuko 千葉大学, 環境健康フィールド科学センター, 講師 (60467686)
• Research Collaborator: Rawal Viresh H. The University of Chicago, Professor
• Project Period (FY): 2014-04-01 – 2018-03-31
• Keywords: 天然物 / 生合成 / インドールアルカロイド / Mitsunobu反応 / インドレニン / パラジウム触媒 / ニトリル / 国際共同研究

Outline of Final Research Achievements

This research project was a chemical study to explore how to efficiently synthesize strictamine which was a phytochemical expected to have a strong effect on cranial nerves. The molecular structure of strictamine has a characteristic skeleton of an indolenine, which is sensitive to many chemical reactions. Therefore, we made a strategy to build the indolenine at the final stage and developed a synthetic route. In addition, we succeeded in developing a novel method, one-carbon homologation of primary alcohols to carboxylic acids, esters, and amides via MAC-Mitsunobu reaction, that achieved its one-pot conversion of two steps instead of conventional four-steps' conversion. Application of this method to industry might result in considerable reduction of efforts and cost.

Free Research Field

有機合成化学