Yang Jin-song
2011
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Journal
Chinese Journal of Synthetic Chemistry
Abstract
(4S,5S,2′R,3′R,2″S)-3-[3′-(N-tert-butoxycarbonyl-2″-pyrrolidinyl)-3′-hydroxy-2′-methylpropanoyl)]-4-methyl-5-phenyl-2-oxazolidinone(6) with three chair center and high stereroslectively was prepared by aldol condensation of(4R,5S)-4-methyl-3-(1-oxopropyl)-5-phenyloxazolidin-2-one and(N-tert-butoxycarbonyl)-S-prolinal.A key synthon of Dolastatin 10,(2R,3R,2′S)-3-(N-tert-butoxycarbonyl-2′-pyrrolidinyl)-methoxyl-2-methylpropanonic acid(Dap),was synthesized by methylation of 3′-OH and dechiral agon in 6.The structures were characterized by 1H NMR,13C NMR,IR and MS.