Total synthesis of uniflorine A, casuarine, australine, 3-epi-australine, and 3,7-di-epi-australine from a common precursor.
A flexible method for the diastereoselective total synthesis of the pyrrolizidine alkaloids uniflorine A, casuarine, australine, and 3-epi-australine and the unnatural epimer 3,7-di-epi-australine from a common chiral 2,5-dihydropyrrole precursor is described.
Ritthiwigrom
Thunwadee
T
School of Chemistry, University of Wollongong, Wollongong, New South Wales, 2522, Australia.
Willis
Anthony C
AC
Pyne
Stephen G
SG
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry*; D011763:Pyrrolizidine Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D007212:Indolizines; D011758:Pyrroles; D011763:Pyrrolizidine Alkaloids; C409108:casuarine; C412020:epiaustraline; C487671:uniflorine A; C059794:australine