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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. Kaduskar
a   Department 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
,
Andrea Pinto
a   Department 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
b   Department of Pharmaceutical Sciences (DISFARM), Università degli Studi di Milano, Via Mangiagalli 25, 20133 Milano, Italy
,
Leonardo Scaglioni
a   Department 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
,
Loana Musso  *
a   Department 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
,
Sabrina Dallavalle
a   Department 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
› Author Affiliations
Further Information

Publication History

Received: 08 June 2017

Accepted after revision: 26 July 2017

Publication Date:
28 August 2017 (online)

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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.

Key words

Streptomyces - antifungal agents - tripeptides - natural products - amino acids - total synthesis

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588553.
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