Synthetic modifications of bifunctional homoallylamines: Synthesis of 2-arylpiperidines, (R)-anatabine and (R)-anabasine. Issue 21 (2nd November 2019)

• Record Type: Journal Article
• Authors: Nallasivam, Jothi L.; Fernandes, Rodney A.
• Is Part Of: Synthetic communications. Volume 49:Issue 21(2019)
• Page Start: 2815
• Page End: 2822
• Publication Date: 2019-11-02
• Subjects: Alkaloids -- anabasine -- anatabine -- homoallylamines -- metathesis -- N-heterocycles; Organic compounds -- Synthesis -- Periodicals; Chemistry, Organic; Synthesis; 547.205
• DOI: 10.1080/00397911.2019.1643890
• Languages: English
• ISSNs: 0039-7911

Abstract

Abstract: The chiral homoallylamines with orthogonal bifunctional handle, an amine, and a pendant allyl unit are available to be easily converted into N -heterocycles. The N -allylation and Ru-catalyzed ring-closing metathesis delivered the bioactive 2-arylpiperidines, Nicotiana tabacum alkaloids ( R )-anatabine and ( R )-anabasine in three steps. A formal synthesis of ( R )- N -methylanatabine and ( R )- N -methylanabasine is also completed. Graphical Abstract: