antofine and tert-butanesulfinamide

antofine has been researched along with tert-butanesulfinamide* in 1 studies

Other Studies

1 other study(ies) available for antofine and tert-butanesulfinamide

ArticleYear
Collective asymmetric synthesis of (-)-antofine, (-)-cryptopleurine, (-)-tylophorine, and (-)-tylocrebrine with tert-butanesulfinamide as a chiral auxiliary.
    The Journal of organic chemistry, 2014, Apr-18, Volume: 79, Issue:8

    A collective asymmetric synthesis of phenanthroindolizidine and phenanthroquinolizidine alkaloids (-)-antofine, (-)-cryptopleurine, (-)-tylophorine, and (-)-tylocrebrine was achieved by means of a reaction sequence involving efficient generation of chiral homoallylic amine intermediates by asymmetric allylation of the corresponding tert-butanesulfinyl imine. From these intermediates, the pyrrolidine and piperidine rings were constructed by means of an intramolecular SN2 substitution reaction and a ring-closing metathesis reaction, respectively. The unusual C5-methoxy-substituted phenanthrene moiety of (-)-tylocrebrine was generated by means of an InCl3-catalyzed cycloisomerization reaction of an o-propargylbiaryl compound.

    Topics: Alkaloids; Butanes; Indoles; Indolizines; Isomerism; Molecular Structure; Phenanthrenes; Phenanthrolines; Stereoisomerism; Sulfonamides

2014