title: Efficient Strategy for the Construction of Both Enantiomers of the Octahydropyrroloquinolinone Ring System: Total Synthesis of (+)-Aspidospermidine.
abstract: An efficient and highly stereoselective intramolecular [3 + 2] cycloaddition of nonstabilized azomethine ylide generated from a designed bicyclic aminal precursor is reported for the synthesis of both (-)- and (+)-octahydropyrroloquinolinone. One of the enantiomers is further advanced to accomplish the total synthesis of (+)-aspidospermidine.
authors.affiliation: Molecular Synthesis and Drug Discovery Laboratory, Centre of Biomedical Research , SGPGIMS Campus, Lucknow 226014, India.
authors.forename: Ganesh
authors.initials: G
authors.lastname: Pandey
authors.affiliation: Molecular Synthesis and Drug Discovery Laboratory, Centre of Biomedical Research , SGPGIMS Campus, Lucknow 226014, India.|Division of Organic Chemistry, CSIR-National Chemical Laboratory , Dr. Homi Bhabha Road, Pune 411008, India.
authors.forename: Shiva Kumar
authors.initials: SK
authors.lastname: Burugu
authors.affiliation: Molecular Synthesis and Drug Discovery Laboratory, Centre of Biomedical Research , SGPGIMS Campus, Lucknow 226014, India.
authors.forename: Pushpendra
authors.initials: P
authors.lastname: Singh
mesh_terms: D002384:Catalysis; D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D015363:Quinolones / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D026121:Indole Alkaloids; D011804:Quinolines; D015363:Quinolones; C409672:aspidospermidine