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Open seminar

Lecture Title "Heterocycles in Natural Product Synthesis"
Date Friday 20 July 2007 15:00
Lecturer Prof. Yoshihisa Kobayashi (Department of Chemistry and Biochemistry, University of California, San Diego)
Place

Seminar Room, the 3rd Floor, Yamate-4
Summary

The presentation will cover the recently progress on natural product synthesis by using novel reagents and methodologies related to unique features of nitrogen-containing heterocycles.
The development of a new convertible isonitrile, indole-isonitrile, for ready access to pyroglutamic acids via an N-acylindole culminated in the formal total synthesis of the proteasome inhibitor omuralide featuring a stereocontrolled Ugi reaction. Indole-Isonitrile was named after the facilitation of hydrolysis of the resulting 2-(2,2-dimethoxyethyl)anilide by Ugi/(Passerini) multi component condensation reaction, via N-acylindole.
A series of biologically intriguing pyroglutamic acids were synthesized in an unprotected form by employing the isonitrile and ammonium acetate in the Ugi 4-center 3-component reaction of gamma-ketoacids. Very recently, the utility of the isonitrile was further elaborated by the discovery of the remarkably simple and mild conversion of aldehydes to alpha-hydroxyacids via N-acylindole.
Currently we are investigating the potential of benzotriazole(Bt)-isonitrile as the next generation of convertible isonitriles for multi-component condensation reaction. New entry of N-acylbenzotriazole was also developed for the hydrolysis of hindered carboxamides by using Goldberg reaction. Those preliminary results will be discussed shortly.
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