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- W2329173280 abstract "We describe a simple and convenient synthesis of the western zone of caprazamycin B using two catalytic asymmetric reactions as key elements of our approach. Desymmetrization of 3-methylglutaric anhydride with the (S)-Ni2-(Schiff base) complex as a catalyst furnished the chiral hemiester, and a thioamide-aldol reaction with mesitylcopper, (R,R)-Ph-BPE, and 2,2,5,7,8-pentamethylchromanol as a catalyst furnished the β-hydroxy thioamide in good yield and enantioselectivity. On further transformation, the thioamide functionality was converted to the corresponding β-hydroxy ester. Finally, a convergent synthesis of the western zone of caprazamycin B was achieved by connecting the hemiester, the β-hydroxy ester, and the 2,3,4-tri-O-methyl-l-rhamnose fragments." @default.
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- W2329173280 date "2012-10-04" @default.
- W2329173280 modified "2023-09-25" @default.
- W2329173280 title "Studies on Catalytic Enantioselective Total Synthesis of Caprazamycin B: Construction of the Western Zone" @default.
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- W2329173280 doi "https://doi.org/10.1021/jo301803h" @default.
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