Concise asymmetric synthesis of (-)-sparteine.
A six-step asymmetric synthesis of natural (-)-sparteine from ethyl 7-iodohept-2-enoate is reported, involving a connective Michael addition of an amino ester-derived enolate to an alpha,beta-unsaturated amino ester.
Hermet
Jean-Paul R
JP
Department of Chemistry, University of York, Heslington, York, UK.
McGrath
Matthew J
MJ
O'Brien
Peter
P
Porter
David W
DW
Gilday
John
J
D000596:Amino Acids / Q000737:chemistry*; D000889:Anti-Arrhythmia Agents / Q000138:chemical synthesis*; D004952:Esters / Q000737:chemistry*; D006536:Heptanes / Q000737:chemistry; D008956:Models, Chemical; D013034:Sparteine / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000596:Amino Acids; D000889:Anti-Arrhythmia Agents; D004952:Esters; D006536:Heptanes; D013034:Sparteine