Total Synthesis and Complete Structural Assignment of Thiocillin I

被引：48

作者：

Aulakh, Virender S. ^{[1
]}

Ciufolini, Marco A. ^{[1
]}

机构：

[1] Univ British Columbia, Dept Chem, Vancouver, BC V6T 1Z1, Canada

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 15期

基金：

加拿大自然科学与工程研究理事会;

关键词：

TOXIC CYCLIC-PEPTIDES; ONE-POT; DIPHENYLPHOSPHORYL AZIDE; THIOPEPTIDE ANTIBIOTICS; ORGANIC-SYNTHESIS; PATELLAMIDES-B; BRONSTED ACID; 1ST SYNTHESIS; AMINO-ACIDS; ALDEHYDES;

D O I：

10.1021/ja110166x

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The total synthesis of the thiopeptide antibiotic, thiocillin I, is described. This work unequivocally defines the full structure (constitution and configuration) of the natural product as 1.

引用

页码：5900 / 5904

页数：5

共 58 条

[21] YB(FOD)3-PROMOTED ENE REACTION OF ALDEHYDES WITH VINYL ETHERS
DEATON, MV
CIUFOLINI, MA
[J]. TETRAHEDRON LETTERS, 1993, 34 (15) : 2409 - 2412
[22] Concise total synthesis of the thiazolyl peptide antibiotic GE2270 A
Delgado, Oscar
Mueller, H. Martin
Bach, Thorsten
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (08) : 2322 - 2339
[23] REACTION OF 4-PYRONES AND CHROMONE WITH CARBANIONS
EIDEN, F
HERDEIS, C
[J]. ARCHIV DER PHARMAZIE, 1977, 310 (09) : 744 - 748
[24] Titanium catalysis in the Ugi reaction of α-amino acids with aromatic aldehydes
Godet, T
Bonvin, Y
Vincent, G
Merle, D
Thozet, A
Ciufolini, MA
[J]. ORGANIC LETTERS, 2004, 6 (19) : 3281 - 3284
[25] PROPOSED STRUCTURE OF THE CYCLIC PEPTIDE DOLASTATIN-3, A POWERFUL CELL-GROWTH INHIBITOR, SHOULD BE REVISED
HAMADA, Y
KOHDA, K
SHIOIRI, T
[J]. TETRAHEDRON LETTERS, 1984, 25 (46) : 5303 - 5306
[26] Recent progress of the synthetic studies of biologically active marine cyclic peptides and depsipeptides
Hamada, Y
Shioiri, T
[J]. CHEMICAL REVIEWS, 2005, 105 (12) : 4441 - 4482
[27] NEW METHODS AND REAGENTS IN ORGANIC-SYNTHESIS .56. TOTAL SYNTHESES OF PATELLAMIDES-B AND PATELLAMIDES-C, CYTO-TOXIC CYCLIC-PEPTIDES FROM A TUNICATE .2. THEIR REAL STRUCTURES HAVE BEEN DETERMINED BY THEIR SYNTHESES
HAMADA, Y
SHIBATA, M
SHIOIRI, T
[J]. TETRAHEDRON LETTERS, 1985, 26 (42) : 5159 - 5162
[28] NEW METHODS AND REAGENTS IN ORGANIC-SYNTHESIS .55. TOTAL SYNTHESES OF PATELLAMIDES-B AND PATELLAMIDES-C, CYTO-TOXIC CYCLIC-PEPTIDES FROM A TUNICATE .1. THEIR PROPOSED STRUCTURES SHOULD BE CORRECTED
HAMADA, Y
SHIBATA, M
SHIOIRI, T
[J]. TETRAHEDRON LETTERS, 1985, 26 (42) : 5155 - 5158
[29] Hausler T., 2006, Viruses vs. Superbugs
[30] Huang L., 1995, HET COMMUN, V1, P335

← 1 2 3 4 5 6 →