Total synthesis of (+)-kalkitoxin.
The neurotoxic lipopeptide (+)-kalkitoxin was synthesized by a route which employed asymmetric organocopper conjugate addition followed by in situ enolate alkylation to install the anti,anti-1,2,4-trimethyl relationship of the toxin; the synthesis of kalkitoxin required sixteen steps and proceeded in 3% overall yield.
White
James D
JD
Department of Chemistry, Oregon State University, Corvallis, OR 97331-4003, USA. james.white@orst.edu
Lee
Chang-Sun
CS
Xu
Qing
Q
D018360:Crystallography, X-Ray; D008055:Lipids / Q000138:chemical synthesis* / Q000737:chemistry; D008074:Lipoproteins / Q000138:chemical synthesis / Q000737:chemistry; D008956:Models, Chemical; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D009498:Neurotoxins / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry
D008055:Lipids; D008074:Lipoproteins; D009498:Neurotoxins; D013844:Thiazoles; C121885:kalkitoxin