Total Synthesis of the Thiazolyl Peptide GE2270 A

Authors


  • This project was supported by the Deutsche Forschungsgemeinschaft (Ba 1372-9), by the Alexander von Humboldt Foundation (research scholarship to O.D.), by the Universität Bayern e.V. (predoctoral scholarship to H.M.M.), and by the Fonds der Chemischen Industrie. We thank Wacker-Chemie (Munich), DSM Fine Chemicals (Linz), and Umicore (Hanau) for the donation of chemicals. The help of Dipl.-Chem. Jochen Klages in recording the NMR spectra is gratefully acknowledged.

Abstract

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When one door closes, another opens: In the synthesis of the thiazolyl peptide GE2270 A (1), the bonds labeled I and II at the pyridine core were established by two consecutive cross-coupling reactions. Amide bond formation (IV) and subsequent intramolecular Stille reaction (III) were more effective than the originally conceived connection strategy (III before IV). GE2270 A (1) was prepared with an overall yield of 4.8 % in 20 steps along the longest linear sequence.

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