Diastereoselective cationic tandem cyclizations to N-heterocyclic scaffolds: total synthesis of (-)-dysibetaine PP.
[reaction: see text] Herein, we report a short and diastereoselective synthesis of the natural product (-)-dysibetaine PP. The key step in the synthetic sequence is a novel highly diastereoselective tandem-cyclization reaction of an enantiomerically pure dipeptide. This cyclization methodology is applied in the synthesis of a broader range of N-heterocyclic scaffolds.
Ijzendoorn
Denis R
DR
Chiralix BV, Nijmegen, The Netherlands.
Botman
Peter N M
PN
Blaauw
Richard H
RH
D000818:Animals; D003500:Cyclization; D004151:Dipeptides / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry; D011760:Pyrrolidinones / Q000138:chemical synthesis*; D013237:Stereoisomerism
D004151:Dipeptides; D011760:Pyrrolidinones; C431075:dysibetaine