Angewandte Chemie - International Edition
Angewandte Chemie - International Edition
5 years ago

Total Synthesis of (−)-N-Methylwelwitindolinone B Isothiocyanate

Total Synthesis of (−)-N-Methylwelwitindolinone B Isothiocyanate
Viresh H. Rawal, Vikram Bhat, Julius R. Reyes, Kenichi Kobayashi, Jiasu Xu
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. Fe it out: Challenges overcome in the synthesis of (−)-N-methylwelwitindolinone B isothiocyanate include stereoselective installation of alkyl chloride and control of the reactivity of the indole unit to oxidants. Pt-catalyzed hydrosilylation prevented unwanted rearrangements, and FeII-catalyzed oxidation facilitated conversion of indole into 2-indolinone.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201705322

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