Chem. J. Chinese Universities ›› 2000, Vol. 21 ›› Issue (3): 391.
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WANG Heng-Shan, JIA Qiang, YANG Xiao-Wu, WANG Rui
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Abstract: From γ-butyrolactone 1, we synthesized (S)-2-methyl-2-nitroethenyl butyrolactone (S)-3 by the mean of direct enantioselective construction of molecule with quaternary carbon stereocenter on the bases of our previous research. (S)-3 was obtained in36% overall yield with 94% optical purity. We established a set of conversions from(±)-3 to the precursor of Vitamin B12 ring Bimide 8 under mild conditions and complete the synthesis of three derivatives of ethosuximide 6_ 8 at the same time. By remolding TiCl3 reduction of nitroolefins the yield of 2-methyl butyrolactone-2-acetaldehyde 4 from 3 can be increased to 88%. Anew method has been found to directly construct succinimide ring from 2-methyl butyrolactone-3-acetic acid 5. The procedure of this conversion is DCCcondensation of 5 and dry benzylamine in acetonitrile catalyzed by DMAPat 0 ℃ over night.
Key words: Chiral quaternary carbon, Vitamin B12 ring-B imide, Succinimide
CLC Number:
O621.3
TrendMD:
WANG Heng-Shan, JIA Qiang, YANG Xiao-Wu, WANG Rui . Studies on the Asymmetric Synthesis of Precursor of Vitamin B12 Ring-B Imide and Succinimide Drugs[J]. Chem. J. Chinese Universities, 2000, 21(3): 391.
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http://www.cjcu.jlu.edu.cn/EN/Y2000/V21/I3/391