Chem. J. Chinese Universities ›› 2000, Vol. 21 ›› Issue (3): 391.

• Articles • Previous Articles     Next Articles

Studies on the Asymmetric Synthesis of Precursor of Vitamin B12 Ring-B Imide and Succinimide Drugs

WANG Heng-Shan, JIA Qiang, YANG Xiao-Wu, WANG Rui   

  1. School of Life Sciences, State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Landzhou 730000, China
  • Received:1999-04-12 Online:2000-03-24 Published:2000-03-24

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: 

TrendMD: