Total synthesis and structural confirmation of the marine natural product dysinosin a: A novel inhibitor of thrombin and factor VIIa

被引：79

作者：

Hanessian, S ^{[1
]}

Margarita, R ^{[1
]}

Hall, A ^{[1
]}

Johnstone, S ^{[1
]}

Tremblay, M ^{[1
]}

Parlanti, L ^{[1
]}

机构：

[1] Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 45期

关键词：

D O I：

10.1021/ja0208153

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The structure and absolute configuration of the marine antithrombotic product dysinosin A was confirmed by total synthesis. The strategy involved disconnections to three subunits, of which two were synthesized from the readily available l-glutamic acid, d-leucine, and d-mannitol. The Grubbs olefin metathesis carbocyclization reaction was utilized to prepare two intermediates. Copyright © 2002 American Chemical Society.

引用

页码：13342 / 13343

页数：2

共 44 条

[1] Armstrong SK, 1998, J CHEM SOC PERK T 1, P371
[2] Practical stereoselective synthesis of conformationally constrained unnatural proline-based amino acids and peptidomimetics
Belvisi, L
Colombo, L
Colombo, M
Di Giacomo, M
Manzoni, L
Vodopivec, B
Scolastico, C
[J]. TETRAHEDRON, 2001, 57 (30) : 6463 - 6473
[3] Synthesis of the octahydroindole core of aeruginosins: A new bicyclic alpha-amino acid
Bonjoch, J
Catena, J
Isabal, E
LopezCanet, M
Valls, N
[J]. TETRAHEDRON-ASYMMETRY, 1996, 7 (07) : 1899 - 1902
[4] Bouma BN, 1998, THROMB HAEMOSTASIS, V80, P24
[5] Improvement in olefin metathesis using a new generation of ruthenium catalyst bearing an imidazolylidene ligand: Synthesis of heterocycles
Briot, A
Bujard, M
Gouverneur, V
Nolan, SP
Mioskowski, C
[J]. ORGANIC LETTERS, 2000, 2 (11) : 1517 - 1519
[6] Dysinosin a:: A novel inhibitor of factor Vila and thrombin from a new genus and species of Australian sponge of the family dysideidae
Carroll, AR
Pierens, GK
Fechner, G
de Almeida Leone, P
Ngo, A
Simpson, M
Hyde, E
Hooper, JNA
Boström, SL
Musil, D
Quinn, RJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (45) : 13340 - 13341
[7] Chiesa MV, 1996, SYNLETT, P441
[8] Intramolecular azomethine ylide cycloaddition reactions to give octahydroindoles
Coldham, I
Crapnell, KM
Moseley, JD
Rabot, R
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (15): : 1758 - 1763
[9] Intramolecular catalysis of amide isomerization:: Kinetic consequences of the 5-NH- -Na hydrogen bond in prolyl peptides
Cox, C
Lectka, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (41) : 10660 - 10668
[10] ENGH R, 1997, Patent No. 97121725

← 1 2 3 4 5 →