Ag(I)-Catalyzed Synthesis of Azabicyclic Alkaloid Frameworks from Ketimine-Tethered Ynones: Total Synthesis of Indolizidine 209D | Zendy

Hon Eong Ho | Zendy; Michael J. James | Zendy; Peter O’Brien | Zendy; Richard J. K. Taylor | Zendy; William P. Unsworth | Zendy

Open Access

Ag(I)-Catalyzed Synthesis of Azabicyclic Alkaloid Frameworks from Ketimine-Tethered Ynones: Total Synthesis of Indolizidine 209D

Author(s) -

Hon Eong Ho,

Michael J. James,

Peter O’Brien,

Richard J. K. Taylor,

William P. Unsworth

Publication year - 2018

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.8b00225

Subject(s) - indolizidine , chemistry , alkaloid , total synthesis , catalysis , stereochemistry , formal synthesis , enantioselective synthesis , combinatorial chemistry , organic chemistry

An efficient Ag(I)-catalyzed π-acid activation method for the cyclization of cyclic ketimine-tethered ynones is reported. Various nitrogen-containing scaffolds commonly found in bioactive alkaloids can be prepared in high yields, and the utility of the method is demonstrated by a formal synthesis of (±)-lasubine II and in a short total synthesis of (±)-indolizidine 209D.

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