Total syntheses of arylindolizidine alkaloids (+)-ipalbidine and (+)-antofine.
This paper presents the first application of two recently developed reactions to natural product synthesis. The first method involves a 6-endo-trig cyclization to prepare a versatile chiral enaminone building block. The second is a direct C-H arylation reaction. As a showcase for the utility of these methods, (+)-antofine and (+)-ipalbidine were synthesized in only 8 steps and 24-26% overall yields.
Niphakis
Micah J
MJ
Department of Medicinal Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, USA.
Georg
Gunda I
GI
D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010618:Phenanthrolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D007211:Indoles; D007212:Indolizines; D010618:Phenanthrolines; C473343:antofine; C057484:ipalbidine