14-Membered cyclodepsipeptides with alternating β-hydroxy and α-amino acids by cyclodimerization

B Iliev, A Linden, R Kunz, H Heimgartner

Index: Iliev, Boyan; Linden, Anthony; Kunz, Roland; Heimgartner, Heinz Tetrahedron, 2006 , vol. 62, # 6 p. 1079 - 1094

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Citation Number: 19

Abstract

The cyclodimerization (twinning) of β-hydroxy acid amides of type under 'direct amide cyclization'(DAC) conditions is described. Although other coupling methods also gave moderate results, best yields were obtained via DAC, reaching 88% for the cyclodimer. In all cases, when starting with racemic material, only the trans-substituted cyclodepsipeptides were isolated. Simple molecular modeling revealed that the formation of the cyclodimer is ...