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Synthesis 2017; 49(02): 391-396
DOI: 10.1055/s-0036-1588355
DOI: 10.1055/s-0036-1588355
paper
Cyclotryptophan Mycotoxins: Short Synthesis of the Desymmetrized meso-Chimonantine Core of Leptosin C
Further Information
Publication History
Received: 14 September 2016
Accepted after revision: 27 October 2016
Publication Date:
01 December 2016 (online)
Dedicated to Professor Dieter Enders on the occasion of his 70th 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.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588355. 1H and 13C NMR spectra as well as MS spectra of all new compounds are included.
- Supporting Information
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