A new solid-phase linker for Suzuki coupling with concomitant macrocyclization:: synthesis of β-turn mimics

被引:71
作者
Li, W [1 ]
Burgess, K [1 ]
机构
[1] Texas A&M Univ, Dept Chem, College Stn, TX 77842 USA
基金
美国国家卫生研究院;
关键词
palladium catalysis; solid-phase syntheses; peptidomimetics; beta-turns;
D O I
10.1016/S0040-4039(99)01306-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The boronic acid linker 12 was prepared and used to produce the beta-turn mimics 1 via a solid-phase Suzuki coupling/macrocyclization/resin-release strategy. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6527 / 6530
页数:4
相关论文
共 12 条
[1]   ORGANOBORANES .31. A SIMPLE PREPARATION OF BORONIC ESTERS FROM ORGANO-LITHIUM REAGENTS AND SELECTED TRIALKOXYBORANES [J].
BROWN, HC ;
COLE, TE .
ORGANOMETALLICS, 1983, 2 (10) :1316-1319
[2]  
COLONGE J, 1954, MEM PRES SOC CHIM, P1454
[3]   Solid-phase SN2 macrocyclization reactions to form β-turn mimics [J].
Feng, YB ;
Pattarawarapan, M ;
Wang, ZC ;
Burgess, K .
ORGANIC LETTERS, 1999, 1 (01) :121-124
[4]   SNAr cyclizations to form cyclic peptidomimetics of β-turns [J].
Feng, YB ;
Wang, ZC ;
Jin, S ;
Burgess, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (41) :10768-10769
[5]   Directed electrophilic cyclizations: Efficient methodology for the synthesis of fused polycyclic aromatics [J].
Goldfinger, MB ;
Crawford, KB ;
Swager, TM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (20) :4578-4593
[6]   Solid-phase Suzuki coupling for C-C bond formation [J].
Guiles, JW ;
Johnson, SG ;
Murray, WV .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (15) :5169-5171
[7]  
Hughes D.L., 1992, ORG REACT, V42, P335, DOI [10.1002/0471264180.OR042.02, DOI 10.1002/0471264180.OR042.02]
[8]   THE USE OF DIETHYL AZODICARBOXYLATE AND TRIPHENYLPHOSPHINE IN SYNTHESIS AND TRANSFORMATION OF NATURAL-PRODUCTS [J].
MITSUNOBU, O .
SYNTHESIS-STUTTGART, 1981, (01) :1-28
[9]   PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOBORON COMPOUNDS [J].
MIYAURA, N ;
SUZUKI, A .
CHEMICAL REVIEWS, 1995, 95 (07) :2457-2483
[10]   The design and synthesis of substituted biphenyl libraries [J].
Pavia, MR ;
Cohen, MP ;
Dilley, GJ ;
Dubuc, GR ;
Durgin, TL ;
Forman, FW ;
Hediger, ME ;
Milot, G ;
Powers, TS ;
Sucholeiki, I ;
Zhou, SL ;
Hangauer, DG .
BIOORGANIC & MEDICINAL CHEMISTRY, 1996, 4 (05) :659-666