Iterative two-step strategy for C2-C4′ linked poly-oxazole synthesis using Suzuki-Miyaura cross-coupling reaction

被引:20
作者
Araki, Hiroshi
Katoh, Tadashi
Inoue, Munenori [1 ]
机构
[1] Tokyo Inst Technol, Dept Elect Chem, Yokohama, Kanagawa 2268502, Japan
[2] Tohoku Pharmaceut Univ, Aoba Ku, Sendai, Miyagi 9818558, Japan
[3] Sagami Chem Res Ctr, Kanagawa 2521193, Japan
关键词
poly-oxazole; Suzuki-Miyaura cross-coupling reaction; iterative synthesis; oxazolylboronate; telomestatin;
D O I
10.1016/j.tetlet.2007.03.109
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An iterative method for the synthesis of C2-C4' linked poly-oxazoles has been developed. This efficient two-step repetitive process includes TBS-iodine exchange reaction and Suzuki-Miyaura cross-coupling reaction with oxazolylboronate 8, which allows appending a bis-oxazole moiety per each iteration. The synthesis of bis-, tris-, tetrakis-, pentakis-, and hexakis-oxazoles (10, 14, 22, 18, and 24) was achieved starting from the common intermediate 7 in 1-5 steps. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3713 / 3717
页数:5
相关论文
共 54 条
[1]   The synthesis of oxazoles by thermolysis or photolysis of 2-acylisoxazol-5-ones [J].
Ang, KH ;
Prager, RH ;
Smith, JA ;
Weber, B ;
Williams, CM .
TETRAHEDRON LETTERS, 1996, 37 (05) :675-678
[2]   Synthesis and reaction of the first oxazol-4-ylboronates: Useful reagents for the preparation of the oxazole-containing biaryl compounds [J].
Araki, H ;
Katoh, T ;
Inoue, M .
SYNLETT, 2006, (04) :555-558
[3]   A two-stage iterative process for the synthesis of poly-oxazoles [J].
Atkins, JM ;
Vedejs, E .
ORGANIC LETTERS, 2005, 7 (15) :3351-3354
[4]   Synthesis of functionalised oxazoles and bis-oxazoles [J].
Bagley, MC ;
Buck, RT ;
Hind, SL ;
Moody, CJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (03) :591-600
[5]  
BARRETT AGM, 1995, SYNLETT, P415
[6]   Asymmetric synthesis of a C1-C19 fragment of ulapualide A [J].
Celatka, CA ;
Panek, JS .
TETRAHEDRON LETTERS, 2002, 43 (39) :7043-7046
[7]   Studies directed toward the synthesis of ulapualide A: Phosphorus-based olefination as model studies for (Schlosser-like) fragment coupling [J].
Celatka, CA ;
Liu, P ;
Panek, JS .
TETRAHEDRON LETTERS, 1997, 38 (31) :5449-5452
[8]   Convergent synthesis of a 24-membered macrocyclic hexaoxazole derivative related to the novel telomerase inhibitor telomestatin [J].
Chattopadhyay, Shital K. ;
Biswas, Suman .
TETRAHEDRON LETTERS, 2006, 47 (45) :7897-7900
[9]   Efficient construction of a doubly functionalized trisoxazole derivative relevant to the synthesis of the novel telomerase inhibitor telomestatin and its analogues [J].
Chattopadhyay, SK ;
Biswas, S ;
Pal, BK .
SYNTHESIS-STUTTGART, 2006, (08) :1289-1294
[10]  
Chattopadhyay SK, 1997, SYNLETT, P1345