Total synthesis of (+)-condylocarpine, (+)-isocondylocarpine, and (+)-tubotaiwine.
The first enantioselective total syntheses of indole alkaloids of the condylocarpine type are reported. (+)-Condylocarpine, (+)-isocondylocarpine, and (+)-tubotaiwine were prepared in high enantiomeric purity (er > 99:1) from (1S,5R)-hexahydro-1,5-methano-1H-azocino[4,3-b]indole-12-one 7b by way of five or six isolated intermediates.
Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, California 92697-2025, USA.
Connor L
CL
Martin
Seiichi
S
Nakamura
Ralf
R
Otte
Larry E
LE
Overman
D000470:Alkaloids / Q000138:chemical synthesis*; D026121:Indole Alkaloids / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism
D000470:Alkaloids; D026121:Indole Alkaloids; C555748:condylocarpine; C555747:isocondylocarpine; C404563:tubotaiwine