Nostalgic review of one student of Prof. Tsuda about natural product, carbanion, thiazoline and β-lactam chemistry

Abstract

This article describes the works of one of Tsuda's students who owes their performance to him through the long-term, direct and indirect influence of the Tsuda school, especially supervised by him during his very last period as a Professor at the University of Tokyo. They consist of i) natural product chemistry, i.e. Siccanin and related congeners, ii) carbanion chemistry, i.e. iodomethylation (C1) and trans-iodopropenylation (C3) reactions using thiazoline derivatives and their synthetic application, and iii) β-lactam chemistry, i.e. 1,3-dipoler cycloaddition reaction of iminochloride of penicillin, new β-lactam ring synthesis, synthesis of carbapenem derivatives including microbial hydration and stereo-specific 1 β-methyl carbapenem synthesis.