An efficient total synthesis of K-13, a non-competitive inhibitor of ACE I

被引:18
作者
Bigot, A [1 ]
Bois-Choussy, M [1 ]
Zhu, JP [1 ]
机构
[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
关键词
D O I
10.1016/S0040-4039(00)00695-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient synthesis of K-13, a non-competitive inhibitor of ACE I, with an endo biaryl ether bond is described. The key cycloetherification reaction of linear tripeptide 10 gave 17-membered macrocycle in quantitative yield. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4573 / 4577
页数:5
相关论文
共 37 条
[11]   A synthetic approach to diaryl ethers using the Robinson annulation [J].
Feng, XQ ;
Edstrom, ED .
TETRAHEDRON-ASYMMETRY, 1999, 10 (01) :99-105
[12]  
ITOKAWA H, 1983, CHEM PHARM BULL, V31, P1424
[13]  
ITOKAWA H, 1984, CHEM PHARM BULL, V32, P284
[14]  
Itokawa H., 1997, ALKALOIDS, V49, P301
[15]   Total synthesis of the cyclic biphenyl ether peptides K-13 and OF4949-III via SNAr macrocyclization of peptidyl ruthenium pi-arene complexes [J].
Janetka, JW ;
Rich, DH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (28) :6488-6495
[16]   Efficient synthesis of selectively protected L-Dopa derivatives from L-tyrosine via Reimer-Tiemann and Dakin reactions [J].
Jung, ME ;
Lazarova, TI .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (05) :1553-1555
[17]   K-13, A NOVEL INHIBITOR OF ANGIOTENSIN-I CONVERTING ENZYME PRODUCED BY MICROMONOSPORA-HALOPHYTICA SUBSP EXILISIA .1. FERMENTATION, ISOLATION AND BIOLOGICAL PROPERTIES [J].
KASE, H ;
KANEKO, M ;
YAMADA, K .
JOURNAL OF ANTIBIOTICS, 1987, 40 (04) :450-454
[18]   Enantioselective synthesis of dityrosine and isodityrosine via asymmetric phase-transfer catalysis. [J].
Lygo, B .
TETRAHEDRON LETTERS, 1999, 40 (07) :1389-1392
[19]  
MORITA H, 1992, CHEM PHARM BULL, V40, P1352, DOI 10.1248/cpb.40.1352
[20]   BIOMIMETIC SYNTHESIS AND STEREOSTRUCTURE OF K-13, A NOVEL INHIBITOR OF ANGIOTENSIN-I CONVERTING ENZYME [J].
NISHIYAMA, S ;
SUZUKI, Y ;
YAMAMURA, S .
TETRAHEDRON LETTERS, 1989, 30 (03) :379-382