Cyclotryptophan Mycotoxins: Short Synthesis of the Desymmetrized meso-Chimonantine Core of Leptosin C

Dedicated to Professor Dieter Enders on the occasion of his 70^th birthday.

Abstract

The desymmetrized meso-chimonantine core of leptosin C was prepared in a short stereoselective convergent sequence in 5 steps as the longest linear path from methyl l-tryptophan hydrochloride as starting material. The key step of this approach was a diastereoselective [4+2] cycloaddition between the bromooxindole and tryptophan derivatives allowing to define the adjacent quaternary benzylic centers in a high chemical yield.

Key words

asymmetric synthesis - mycotoxins - alkaloids - cycloadditions - tandem reaction

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