The first enantioselective synthesis of cytotoxic marine natural product palau'imide and assignment of its C-20 stereochemistry.
Methyl tetramate derivative 6 has been developed as a new building block for the flexible and racemization-free synthesis of methyl 5-benzyl-3-methyltetramate via alkylation, and used in the first asymmetric synthesis of palau'imide (1). This allowed the establishment of the hitherto unknown stereochemistry at the C-20 of palau'imide as S.
Lan
Hong-Qiao
HQ
Department of Chemistry and The Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, PR China.
Ruan
Yuan-Ping
YP
Huang
Pei-Qiang
PQ
D001554:Benzene / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis*; D007094:Imides / Q000138:chemical synthesis*; D015394:Molecular Structure; D009842:Oligopeptides / Q000138:chemical synthesis*; D011758:Pyrroles / Q000138:chemical synthesis*; D013237:Stereoisomerism
D001688:Biological Products; D007094:Imides; D009842:Oligopeptides; D011758:Pyrroles; C552389:palau'imide; D001554:Benzene