Quick assembly of 1-alkylidenyl-tetrahydroisoquinolines via a Catellani reaction/NBS-mediated cyclization sequence and synthetic applications

We herein disclose a modular synthesis of 1-bromomethylene-THIQs involving a Catellani reaction of aryl iodides, aziridines, and terminal alkynes followed by an N -bromosuccinimide (NBS)-mediated cyclization. This approach features mild reaction conditions, wide substrate scope, good step-economy an...

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Veröffentlicht in:Science China. Chemistry 2023-11, Vol.66 (11), p.3136-3140
Hauptverfasser: Jia, Shihu, Bai, Miao, Zhou, Siwei, Sheng, Ruiqing, Cheng, Hong-Gang, Zhou, Qianghui
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Sprache:eng
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Zusammenfassung:We herein disclose a modular synthesis of 1-bromomethylene-THIQs involving a Catellani reaction of aryl iodides, aziridines, and terminal alkynes followed by an N -bromosuccinimide (NBS)-mediated cyclization. This approach features mild reaction conditions, wide substrate scope, good step-economy and good scalability. Based on this new method, we have accomplished the concise total synthesis of (±)-cularine, formal synthesis of 8-oxopseudopalmatine as well as the first total synthesis of dactyllactone A, demonstrating the wide synthetic potential of this method.
ISSN:1674-7291
1869-1870
DOI:10.1007/s11426-022-1526-7