Regioselective and Stereoselective Reductive Aziridinium Ring Cleavage Leading to Azabicyclodecane Architecture: Enantioselective Synthesis of (+)-Subincanadine F

The Journal of Organic Chemistry
Manojkumar G Kalshetti, Narshinha P Argade

Abstract

Enantioselective synthesis of cytotoxic indole alkaloid (+)-subincanadine F was accomplished starting from the corresponding ( S)-acetoxysuccinimide via aziridinium ring formation and its reductive ring expansion route. Regioselective and stereoselective reductive aziridinium carbon-nitrogen bond cleavage comprising ring expansions was a key step. The ( S)-OMOM protection of the hydroxyl moiety adjacent to a benzylic carbon of an in situ formed aziridinium system was necessary for lithium borohydride-induced reductive ring expansions, and it also served as a latent source of an essential ketone carbonyl group for the generation of an α,β-conjugated system.

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Citations

Dec 24, 2018·Organic & Biomolecular Chemistry·Manojkumar G Kalshetti, Narshinha P Argade
Jun 27, 2019·Organic & Biomolecular Chemistry·Santosh V Shelar, Narshinha P Argade

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