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1. Biology- and Diversity-Oriented Domino Reactions for Synthesis of AMPA Receptor Antagonist IKM-159 and Analogues

Author

Masato Oikawa, Yuuki Kasori, Etsuko Murakami, Yuya Oikawa, Yuichi Ishikawa, and Lisa Katayama

Subjects
chemistry.chemical_compound, Natural product, chemistry, Cascade reaction, Stereochemistry, Organic Chemistry, Salt metathesis reaction, Antagonist, AMPA receptor, Selective antagonist, Metathesis, Catalysis, Domino
Abstract

By natural product inspired diversity-oriented synthesis, we had developed a new class of selective antagonist, IKM-159, for the AMPA receptor. Here, we report syntheses of IKM-159 and skeletally diverse five analogues in racemic forms, two of which are heterotricycles and the other three compounds are truncated analogues, to study the structure–activity relationships. The key reactions are two domino reactions including Ugi/Diels–Alder reaction and domino metathesis reaction. An exceptionally high level of regiocontrol in the cross metathesis reaction is also reported.

Published
2013

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