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Stereoselective Synthesis of (−)-Chloramphenicol, (+)-Thiamphenicol and (+)-Sphinganine via Chiral Tricyclic Iminolactone

  1. Qiong Li1,2,
  2. Hongbo Zhang1,
  3. Chenguang Li1,
  4. Pengfei Xu1,*

Article first published online: 27 DEC 2012

DOI: 10.1002/cjoc.201201093

Issue

Chinese Journal of Chemistry

Chinese Journal of Chemistry

Special Issue: Dedicated to the Memory of Professor Wei-Shan Zhou

Volume 31, Issue 1, pages 149–153, January, 2013

Additional Information

How to Cite

Li, Q., Zhang, H., Li, C. and Xu, P. (2013), Stereoselective Synthesis of (−)-Chloramphenicol, (+)-Thiamphenicol and (+)-Sphinganine via Chiral Tricyclic Iminolactone. Chin. J. Chem., 31: 149–153. doi: 10.1002/cjoc.201201093

Author Information

  1. 1

    State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu 730000, China

  2. 2

    College of Pharmacy, Lanzhou University, Lanzhou, Gansu 730000, China

*State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu 730000, China, Tel.: 0086-0931-8912281; Fax: 0086-0931-8915557

Publication History

  1. Issue published online: 18 JAN 2013
  2. Article first published online: 27 DEC 2012
  3. Manuscript Accepted: 30 NOV 2012
  4. Manuscript Received: 7 NOV 2012

Funded by

  • the National Basic Research Program of China. Grant Number: 2011CB833200
  • the National Natural Science Foundation of China. Grant Number: 20772051, 20972058
  • the "111" Program from MOE of P. R. China
  • the Fundamental Research Funds for the Central Universities. Grant Number: lzujbky-2012-90

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Keywords:

  • β-hydroxy-α-amino alcohol;
  • tricyclic iminolactone;
  • total synthesis

Abstract

The stereoselective syntheses of (−)-chloramphenicol, (+)-thiamphenicol and (+)-sphinganine are described. The two continuous chiral centers within three target molecules were constructed through aldol reaction of chiral tricyclic iminolactone and aldehyde.

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