Efficient synthetic access to the hetisine C20-diterpenoid alkaloids. A concise synthesis of nominine via oxidoisoquinolinium-1,3-dipolar and dienamine-Diels-Alder cycloadditions.
A concise synthetic approach to the hetisine C20-diterpenoid alkaloids is reported. The total synthesis of (+/-)-nominine was accomplished in a 15-step sequence employing a dual cycloaddition strategy. Key features of the synthesis include a reversible intramolecular 4-oxidoisoquinolinium betaine dipolar cycloaddition in conjunction with a pyrrolidine-induced dienamine isomerization/Diels-Alder cascade.
Peese
Kevin M
KM
Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA.
Gin
David Y
DY
D031841:Aconitum / Q000737:chemistry*; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000588:Amines / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007546:Isoquinolines / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
D000470:Alkaloids; D000588:Amines; D004224:Diterpenes; D007211:Indoles; D007546:Isoquinolines; C473425:nominine