Synthesis 2017; 49(24): 5351-5356
DOI: 10.1055/s-0036-1588553
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of the Tripeptide Antibiotic Resormycin

Rahul D. Kaduskara, Andrea Pintoa, b, Leonardo Scaglionia, Loana Musso*a, Sabrina Dallavallea
  • aDepartment of Food, Environmental and Nutritional Sciences, Division of Chemistry and Molecular Biology, Università degli Studi di Milano, Via Celoria 2, 20133 Milano, Italy   Email: loana.musso@unimi.it
  • bDepartment of Pharmaceutical Sciences (DISFARM), Università degli Studi di Milano, Via Mangiagalli 25, 20133 Milano, Italy
Further Information

Publication History

Received: 08 June 2017

Accepted after revision: 26 July 2017

Publication Date:
28 August 2017 (eFirst)

Abstract

A short and efficient synthesis of resormycin, a metabolite of Streptomyces platensis MJ953-SF5 with herbicidal and antifungal activity, is described. The key step in our synthetic approach is a late-stage stereospecific dehydration of a β-hydroxy amino acid to install the Z-olefin. Because of the modular nature of the synthesis, access to analogues for biological evaluation is readily available.

Supporting Information

 
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