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Updated: Apr 17, 2026

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Published on: April 9, 2018
TMSOTf-Mediated Cascade Synthesis of Hexahydropyrrolo[2,3-b]indoline Frameworks via the Meyer-Schuster Rearrangement
Shubham C Rivonker1,2, Vinay Kumar Sthalam1,2, Ashok Kale2
1BK21 FOUR Team and Integrated Research Institute for Drug Development, College of Pharmacy, Dongguk University, 10326 Goyang,Republic of Korea.
Abstract:
TMSOTf-promoted cascade reaction between protected tryptamine and propargyl alcohol has been developed as an efficient strategy for the construction of hexahydropyrrolo[2,3-b]indoline frameworks. The transformation enables access to an expanded chemical space around this important scaffold via a Lewis-acid-driven annulation strategy. The protocol proceeds through a Meyer-Schuster rearrangement, followed by regioselective C-3 nucleophilic addition of the indole ring and subsequent 5-exo-trig cyclization. This method affords structurally diverse hexahydropyrrolo[2,3-b]indolines in moderate to good yields.
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