Chem. J. Chinese Universities ›› 2001, Vol. 22 ›› Issue (12): 2045.

• Articles • Previous Articles     Next Articles

Design of a Novel Macrocyclic Sulfonamide Peptidomimetics and Synthesis of the Precursors

ZHAO BaoXiang1, Siegfried Blechert2   

  1. 1. School of Chemistry & Chemical Engineering, Shandong University, Jinan 250100, China;
    2. Institutfur Organische Chemie, Sekr.TC2, Technische Universitat Berlin, Straedes 1
    7. Juni 135, D-10623, Germany
  • Received:2000-09-22 Online:2001-12-24 Published:2001-12-24

Abstract: Aroute of synthesis of a novel macrocyclic sulfonamide peptidomimetics via ring closing metathesis(RCM) has been designed. Allyl glutaric anhydride has been synthesized from commercially available diethyl allylmanolate and tert butyl acrylate by the Michael reaction and hydrolysis followed by decarboxylation and dehydration. Then, allyl hydrogen2allylglutarate, a precursor for RCM, has been prepared. The synthesis of N-allyl-ethoxycarbonyl-aminoethylsulfonyl amide, another precursor, has been accomplished from cystine.

Key words: Sulfonamide peptidomimetics, Michael reaction, Allyl glutaric anhydride, Allyl hydrogen 2 allylglutarate, N-Allyl-2-ethoxycarbonyl-2-amino ethylsulfonyl amide

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