Total synthesis of TAK-kinase inhibitor LL-Z1640-2 via consecutive macrocyclization and transannular aromatization.
The biomimetic total synthesis of LL-Z1640-2 (3) is reported without the use of phenol protection. The aromatic unit was constructed via the transannular aromatization of macrocyclic triketo-ester 2, which in turn was synthesized by macrolactonization using an intramolecular trapping of a triketo-ketene derived from dioxinone 1.
Department of Chemistry, Imperial College, London SW7 2AZ, England.
Hideki
H
Miyatake-Ondozabal
Anthony G M
AG
Barrett
D003500:Cyclization; D004148:Dioxolanes / Q000138:chemical synthesis; D007783:Lactones / Q000138:chemical synthesis*; D020930:MAP Kinase Kinase Kinases / Q000037:antagonists & inhibitors*; D015394:Molecular Structure; D047428:Protein Kinase Inhibitors / Q000138:chemical synthesis*; D000099151:MAP Kinase Kinase Kinase 7
D004148:Dioxolanes; D007783:Lactones; D020930:MAP Kinase Kinase Kinases; D047428:Protein Kinase Inhibitors; D000099151:MAP Kinase Kinase Kinase 7; C118715:LL Z1640-2; C010962:formal glycol