Concise total synthesis of the thiazolyl peptide antibiotic GE2270 A

O Delgado, HM Müller, T Bach

Index: Delgado, Oscar; Martin Mueller; Bach, Thorsten Chemistry - A European Journal, 2008 , vol. 14, # 8 p. 2322 - 2339

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Citation Number: 48

Abstract

Abstract The potent antibiotic thiazolylpeptide GE2270 A was synthesized starting from N- tert-butyloxycarbonyl protected valine in a longest linear sequence of 20 steps and with an overall yield of 4.8%. Key strategy was the assembly of the 2, 3, 6-trisubstituted pyridine core by consecutive cross-coupling reactions starting from 2, 6-dibromo-3-iodopyridine. The complete Southern fragment was installed by Negishi cross-coupling of 3-zincated 2, 6- ...