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. 2017 Aug 7;56(33):9962-9966.
doi: 10.1002/anie.201705322. Epub 2017 Jul 12.

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

Julius R Reyes  1 , Jiasu Xu  1 , Kenichi Kobayashi  1 , Vikram Bhat  1 , Viresh H Rawal  1
Affiliations

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

Julius R Reyes et al. Angew Chem Int Ed Engl. .

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.

Keywords: alkaloids; natural products; oxidation; total synthesis; welwitindolinones.

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