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

Julius R Reyes; Jiasu Xu; Kenichi Kobayashi; Vikram Bhat; Viresh H Rawal

doi:10.1002/anie.201705322

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

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

Authors

Julius R Reyes¹, Jiasu Xu¹, Kenichi Kobayashi¹, Vikram Bhat¹, Viresh H Rawal¹

Affiliation

¹ Department of Chemistry, University of Chicago, 5735 South Ellis Avenue, Chicago, IL, 60637, USA.

PMID: 28700100
DOI: 10.1002/anie.201705322

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 Fe^II -catalyzed oxidation accomplished the problematic conversion of indole into 2-indolinone.

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

Publication types

Research Support, Non-U.S. Gov't