A five-step synthesis of (±)-tylophorine via a nitrile-stabilized ammonium ylide.
The Stevens rearrangement of a nitrile-stabilized ammonium ylide is the key step of a very short and practical synthesis of the phenanthroindolizine alkaloid (±)-tylophorine. The method requires only five linear steps and is devoid of any protecting group manipulations.
Institute of Organic Chemistry, University of Mainz, Duesbergweg 10-14, D-55128 Mainz, Germany.
Günther
G
Lahm
Alexander
A
Stoye
Till
T
Opatz
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D010616:Phenanthrenes / Q000138:chemical synthesis* / Q000737:chemistry; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*
D000470:Alkaloids; D007212:Indolizines; D009570:Nitriles; D010616:Phenanthrenes; D000644:Quaternary Ammonium Compounds; C004218:tylophorine