Total synthesis of (+/-)-jamtine using a thionium/N-acyliminium ion cascade.
[reaction: see text] The first total synthesis of (+/-)-jamtine (4), a tetrahydroisoquinoline alkaloid reputed for its therapeutic properties, is described. The key step involves a tandem thionium/N-acyliminium ion cyclization from enamido sulfoxide 13. The cascade process takes place with high diastereoselectivity and in excellent yield.
Padwa
Albert
A
Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA. chemap@emory.edu
Danca
M Diana
MD
D000470:Alkaloids / Q000138:chemical synthesis*; D000890:Anti-Infective Agents / Q000138:chemical synthesis*; D002208:Caproates / Q000737:chemistry; D007546:Isoquinolines / Q000138:chemical synthesis*; D007783:Lactones / Q000737:chemistry; D010946:Plants, Medicinal; D000644:Quaternary Ammonium Compounds / Q000737:chemistry
D000470:Alkaloids; D000890:Anti-Infective Agents; D002208:Caproates; D007546:Isoquinolines; D007783:Lactones; D000644:Quaternary Ammonium Compounds; C467072:jamtine; C121056:caprolactone; C059915:thionium