Total synthesis of (+)-batzelladine A and (-)-batzelladine D via [4 + 2]-annulation of vinyl carbodiimides with N-alkyl imines.
A diastereoselective [4 + 2]-annulation of vinyl carbodiimides with chiral N-alkyl imines has been developed to access the stereochemically rich polycyclic guanidine cores of the batzelladine alkaloids. Application of this strategy, together with additional key steps such as long-range directed hydrogenation and diastereoselective intramolecular iodo-amination, led to highly convergent total syntheses of (-)-batzelladine D and (+)-batzelladine A with excellent stereocontrol.
Arnold
Michael A
MA
Department of Chemistry, University of Illinois, Urbana, 61801, USA.
Day
Kenneth A
KA
Durón
Sergio G
SG
Gin
David Y
DY
D000470:Alkaloids / Q000138:chemical synthesis*; D002234:Carbodiimides / Q000737:chemistry*; D006146:Guanidines / Q000138:chemical synthesis*; D007097:Imines / Q000737:chemistry*; D011743:Pyrimidines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000470:Alkaloids; D002234:Carbodiimides; D006146:Guanidines; D007097:Imines; D011743:Pyrimidines; C438977:batzelladine A; C410707:batzelladine D