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Title: Economical route for oxidative cleavage of double bond to synthesize taxol side chain
Authors: Bhatia, Sumati
Singh, Sukhdev
Kumar, Rajesh
Kumar, Amit
Olsen, Carl E
Prasad, Ashok K
Issue Date: Mar-2013
Publisher: NISCAIR-CSIR, India
Abstract: An efficient, economical and industry-friendly methodology has been developed for the synthesis of C-13 side chain of taxol, (2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoic acid by oxidative cleavage of alkene precursor N-[(1S,2S)-2-(1-ethoxyethoxy)-1-phenylbut-3-en-1-yl]benzamide using KMnO4-NaIO4-K2CO3 as oxidant in acetone-water in much higher yields of 80% than the conventional RuCl3-NaIO4 method. Further, the developed methodology has been successfully used for the synthesis of O-acetylated taxotere side chain (2R,3S)-2-acetoxy-3-[N-(tert-butoxycarbonyl)amino]-3-phenylpropanoic acid and taxol side chain analogues (2R,3S)- 2-acetoxy-3-(4′′-chloro- / 4′′-fluoro- / 4′′-trifluoromethyl-benzamido)-3-phenylpropanoic acid from their corresponding alkene precursor, which demonstrate the generality of the developed oxidative cleavage methodology.
Page(s): 379-386
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.52B(03) [March 2013]

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