Novel polyoxazole-based cyclopeptides from Streptomyces sp. Total synthesis of the cyclopeptide YM-216391 and synthetic studies towards telomestatin

J Deeley, A Bertram, G Pattenden

Index: Deeley, Jon; Bertram, Anna; Pattenden, Gerald Organic and Biomolecular Chemistry, 2008 , vol. 6, # 11 p. 1994 - 2010

Full Text: HTML

Citation Number: 44

Abstract

A convergent, complementary, synthetic approach to the contiguously linked tris-oxazole units 10, 11 and 12 in telomestatin (1) and YM-216391 (2) is described. The route involves coupling reactions between oxazole 4-carboxylic acids, viz16a, 16c, 16d and oxazole 2- substituted methylamines, viz16b, 16e, 17, leading to the amides 18 and 21, followed by cyclodehydrations to the corresponding bis-oxazole oxazolines, eg 19, and oxidations of ...