Diastereoselective [4+2] annulation of vinyl carbodiimides with N-alkyl imines. Asymmetric synthetic access to the batzelladine alkaloids.
A diastereoselective [4+2] annulation of vinyl carbodiimides with chiral N-alkyl imines has been developed to access the stereochemically rich tricyclic core of the batzelladine alkaloids. Its application to the asymmetric synthesis of batzelladine D permitted the use of long-range, directed hydrogenation and stereoselective intramolecular iodoamination as additional key steps to establish the remaining stereocenters within the natural product with excellent stereocontrol.
Arnold
Michael A
MA
Department of Chemistry, University of Illinois, Urbana, IL 61801, USA.
Durón
Sergio G
SG
Gin
David Y
DY
D000470:Alkaloids / Q000138:chemical synthesis*; D000478:Alkylation; D002234:Carbodiimides / Q000737:chemistry*; D019791:Guanidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D006146:Guanidines / Q000138:chemical synthesis; D007097:Imines / Q000737:chemistry*; D011743:Pyrimidines / Q000138:chemical synthesis; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
D000470:Alkaloids; D002234:Carbodiimides; D006146:Guanidines; D007097:Imines; D011743:Pyrimidines; D014753:Vinyl Compounds; C438977:batzelladine A; C410707:batzelladine D; C444860:batzelladine F; D019791:Guanidine