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Title: Stereoselective synthesis of subincanadine alkaloids framework
Authors: Kalshetti, Manojkumar G
Argade, Narshinha P
Keywords: (S)-Acetoxysuccinimide;Grignard reaction;Stereoselective Pictet‒Spengler cyclization;Alane reduction;PCC-oxidation;Condensation;Indolizinoindolone
Issue Date: Jun-2019
Publisher: NISCAIR-CSIR, India
Abstract: Starting from N-tosyltryptamine and (S)-acetoxysuccinic anhydride, a facile synthesis of (‒)-indolizinoindolone has been demonstrated as a basic structural outline of bioactive subincanadine alkaloids. Regioselective Grignard reaction with (S)-acetoxysuccinimide, stereoselective intramolecular cyclization to form (‒)-indolizinoindolone skeleton and TiCl4 induced condensation with acetaldehyde for stereoselective generation of exocyclic carbon‒carbon double bond are the key features.
Page(s): 669-673
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.58B(06) [June 2019]

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