Total Synthesis of (-)-N-Methylwelwitindolinone B Isothiocyanate
Julius R Reyes1, Jiasu Xu1, Kenichi Kobayashi1
1Department of Chemistry, University of Chicago, 5735 South Ellis Avenue, Chicago, IL, 60637, USA.
Abstract:
The asymmetric synthesis of (-)-N-methylwelwitindolinone B isothiocyanate is reported. Critical challenges overcome through these studies include the stereoselective installation of the sterically congested C13 alkyl chloride and control of the wayward reactivity of the indole unit to standard oxidants. A Pt-catalyzed hydrosilylation helped stymie unwanted rearrangements facilitated by vinyl group participation during the chloride installation step, and a new FeII -catalyzed oxidation accomplished the problematic conversion of indole into 2-indolinone.
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