Enantio- and stereoselective route to the phoslactomycin family of antibiotics: formal synthesis of (+)-fostriecin and (+)-phoslactomycin B.
A general methodology applicable for the synthesis of the phoslactomycin family of antibiotics, potent and selective protein phosphatase inhibitors, has been developed starting from a beta-isocupreidine-catalyzed asymmetric Baylis-Hillman reaction of 3-(4-methoxybenzyloxy)propanal with hexafluoroisopropyl acrylate, and thereby formal syntheses of (+)-fostriecin and (+)-phoslactomycin B have been accomplished.
Graduate School of Biomedical Sciences, Nagasaki University, Nagasaki 852-8521, Japan.
Shaheen M
SM
Sarkar
Everlyne N
EN
Wanzala
Setsuya
S
Shibahara
Keisuke
K
Takahashi
Jun
J
Ishihara
Susumi
S
Hatakeyama
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D006912:Hydroxyquinolines / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000138:chemical synthesis / Q000737:chemistry; D011090:Polyenes; D054645:Protein Phosphatase 1 / Q000037:antagonists & inhibitors / Q000378:metabolism; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D011812:Quinuclidines / Q000737:chemistry; D013237:Stereoisomerism
D000475:Alkenes; D000900:Anti-Bacterial Agents; D004791:Enzyme Inhibitors; D006912:Hydroxyquinolines; D007783:Lactones; D009943:Organophosphorus Compounds; D011090:Polyenes; D011753:Pyrones; D011812:Quinuclidines; C517075:beta-isocupreidine; C060449:phoslactomycin B; D054645:Protein Phosphatase 1; C040313:fostriecin