Development of one-pot synthesis of 3a-subsituted pyrroloindole and exhaustive synthesis of associated biologically active natural products

2015 Fiscal Year Final Research Report

• Project/Area Number: 25860014
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Chemical pharmacy
• Research Institution: Meiji Pharmaceutical University
• Principal Investigator: Tayu Masanori 明治薬科大学, 薬学部, 助手 (20632780)
• Project Period (FY): 2013-04-01 – 2016-03-31
• Keywords: インドール / 天然物合成 / 不斉合成 / C2対称性 / スルホキシド

Outline of Final Research Achievements

DMSO/Tf2O Mediated one-pot construction of 3a-substituted pyrroloindole framework has been developed. In investigation of a variety of nucleophiles, the synthetic method of 3-(1-indolyl)pyrroloindole framework with indoline nucleus has been developed, which was applied in total synthesis of (±)-psychotriasine.
In the case of tryptamine nucleophile, one-pot synthesis of bisquaternary carbon containing bispyrroloindole core has been achieved. Furthermore, the first one-pot heterodimerization has been successfully developed with tryptamine derivative which was different from starting one.
In addition, enantioselective synthetic method has been achieved with newly designed C2-symmetric chiral sulfoxide. The synthetic utility of this method was declared through the enantioselective total synthesis of (+)-psychotriasine.

Free Research Field

有機化学