Asymmetric total synthesis of apratoxin D.
The first asymmetric total synthesis of the marine natural product apratoxin D, a highly potent inhibitor of H-460 human lung cancer cell growth (IC(50) value of 2.6 nM), is described. Asymmetric N-amino cyclic carbamate (ACC) α,α-bisalkylation was utilized to establish the isolated C-37 methyl group with excellent selectivity. Other key asymmetric transformations employed were an Evans syn-aldol and a Paterson anti-aldol, both of which also proceeded with excellent stereoselectivity.
Department of Chemistry, University of Houston, Houston, Texas 77204-5003, USA.
Bradley D
BD
Robertson
Sarah E
SE
Wengryniuk
Don M
DM
Coltart
D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D047630:Depsipeptides / Q000138:chemical synthesis* / Q000494:pharmacology; D006801:Humans; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D047630:Depsipeptides; C531298:apratoxin D