Cyclotryptophan Mycotoxins: Short Synthesis of the Desymmetrized meso-Chimonantine Core of Leptosin C
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Date
2016-12-01Author
Olaizola Alvarez, Yurre
Abdine, R. A. A.
Dhimane, Hamid
Dalko, Peter I.
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Synthesis 49(2) : 391-396 (2017)
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.