Four-Step Total Synthesis of (+)-Euphococcinine and (±)-Adaline

A four-step enantiospecific total synthesis of bicyclic homotropinone alkaloid euphococcinine and a racemic synthesis of adaline were reported. Key reactions in the synthesis are the diastereoselective addition of a Wittig phosphorene to the ketimines derived from Davis–Ellman sulfinamides, ring-clo...

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Veröffentlicht in:Journal of organic chemistry 2021-09, Vol.86 (17), p.12285-12291
Hauptverfasser: Khandare, Sopan P, Prasad, Kavirayani R
Format: Artikel
Sprache:eng
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Zusammenfassung:A four-step enantiospecific total synthesis of bicyclic homotropinone alkaloid euphococcinine and a racemic synthesis of adaline were reported. Key reactions in the synthesis are the diastereoselective addition of a Wittig phosphorene to the ketimines derived from Davis–Ellman sulfinamides, ring-closing metathesis, and intramolecular Michael reactions.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c00938