Synthesis of cyclic dipeptides by ring-closing metathesis

被引：0

作者：

Reichwein, JF ^{[1
]}

Liskamp, RMJ ^{[1
]}

机构：

[1] Univ Utrecht, Inst Pharmaceut Sci, Dept Med Chem, NL-3508 TB Utrecht, Netherlands

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 2000卷 / 12期

关键词：

ring closure; metathesis; peptides; peptidomimetics; cyclization; dienes;

D O I：

10.1002/1099-0690(200006)2000:12<2335::AID-EJOC2335>3.0.CO;2-C

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several cyclic dipeptides (4a-g and 9a-c) have been synthesized by "amide-to-amide" cyclization of 2a-g and 8a-c, respectively, by means of ring-closing metathesis employing the Grubbs ruthenium catalyst. The influence of additives as well as the length of the amide substituent were studied. Best yields were obtained by cyclization in solution with either lithium fluoroacetate or alpha,alpha-dichlorotoluene as an additive.

引用

页码：2335 / 2344

页数：10

共 50 条

[31] Synthesis of Berkeleylactone A by Ring-Closing Alkyne Metathesis
Schmidt, Frank
Ammanath, Aparna Viswanathan
Goetz, Friedrich
Maier, Martin E.
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (36)
[32] Synthesis of vinyl fluorides by ring-closing metathesis
Marhold, M
Buer, A
Hiemstra, H
van Maarseveen, JH
Haufe, G
[J]. TETRAHEDRON LETTERS, 2004, 45 (01) : 57 - 60
[33] Synthesis of Macrocyclic β-Peptidomimetics by Ring-Closing Metathesis
Dinh Hieu Tran
Xuan Tu Nguyen
Thi Minh Chau Tran
Thuy Quynh Le
Chang Ho Oh
Dinh Hung Mac
[J]. CHEMISTRYSELECT, 2020, 5 (39): : 12232 - 12235
[34] Synthesis of cyclic proline-containing peptides via ring-closing metathesis
Harris, PWR
Brimble, MA
Gluckman, PD
[J]. ORGANIC LETTERS, 2003, 5 (11) : 1847 - 1850
[35] Synthesis of Cyclic Peptides through Ring-Closing Metathesis of Photolabile Protecting Groups
Hoffmann, Judith
Kazmaier, Uli
[J]. SYNTHESIS-STUTTGART, 2015, 47 (03): : 411 - 420
[36] Ring-Closing Metathesis Approaches for the Solid-Phase Synthesis of Cyclic Peptoids
Khan, Sharaf Nawaz
Kim, Arim
Grubbs, Robert H.
Kwon, Yong-Uk
[J]. ORGANIC LETTERS, 2011, 13 (07) : 1582 - 1585
[37] A highly efficient and practical synthesis of cyclic phosphinates using ring-closing metathesis
Bujard, M
Gouverneur, V
Mioskowski, C
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (06): : 2119 - 2123
[38] SYNTHESIS OF CYCLIC POLY(ε-CAPROLACTONE) BY HIGH EFFICIENT RING-CLOSING METATHESIS REACTION
Chen, Lei-yan
Xu, Bo-lin
Li, Meng
Li, Hai-ying
[J]. ACTA POLYMERICA SINICA, 2012, (07) : 743 - 748
[39] Ring-closing metathesis in peptides
Gleeson, Ellen C.
Jackson, W. Roy
Robinson, Andrea J.
[J]. TETRAHEDRON LETTERS, 2016, 57 (39) : 4325 - 4333
[40] Ring-closing olefin metathesis
不详
[J]. NACHRICHTEN AUS CHEMIE TECHNIK UND LABORATORIUM, 1995, 43 (7-8): : 809 - +

← 1 2 3 4 5 →