若干重要生理活性天然产物的化学与生物学研究:Total synthesis of salinamide A, a potent anti-inflammatory ...

  • 关键字: salinamide A 发布者:Tan Li, and Dawei Ma* 发布时间:2009-03-02 18:03:02 点击数: 8483次

Angew. Chem. Int. Ed. 2008, 47, 3614-3617.
Total synthesis of salinamide A, a potent anti-inflammatory bicyclic depsipeptide
Tan Li, and Dawei Ma*
State Key Laboratory of Bioorganic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Abstract: The first total synthesis of potent anti-inflammatory agent salinamide A was achieved. Its phenylglycine-derived epoxide fragment was elaborated via ring opening of an epoxide with a 4-hydroxyphenylglycine derivative (to create aryl alkyl ether bond) and subsequent chain elongation. After introducing required amino acid residues, this molecule was finally assembled via first macrolactamization at the Ile-Thr site and second macrolactamization at the glycine and a,b-unsaturated acid. The overall yield is about 1% for 28 linear steps.