Total Synthesis and Stereochemical Reassignment of Bisebromoamide

被引：56

作者：

Gao, Xuguang ^{[1
]}

Liu, Yuqing ^{[2
]}

Kwong, Shuqin ^{[2
]}

Xu, Zhengshuang ^{[1
,2
]}

Ye, Tao ^{[1
,2
]}

机构：

[1] Univ Town Shenzhen, Shenzhen Grad Sch, Peking Univ, Lab Chem Genom, Shenzhen 518055, Peoples R China

[2] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Kowloon, Hong Kong, Peoples R China

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 13期

关键词：

COUPLING REAGENT; MARINE CYANOBACTERIA; PEPTIDE; POTENT; 1-HYDROXY-7-AZABENZOTRIAZOLE; METABOLITES; ACID;

D O I：

10.1021/ol101021v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A revised configurational assignment for the thiazoline moiety of the marine peptide bisebromoamide is proposed and validated by total synthesis.

引用

页码：3018 / 3021

页数：4

共 43 条

[1] Facile cleavage of Si-C bonds during the sol-gel hydrolysis of aminomethyltrialkoxysilanes - A new method for the methylation of primary amines [J].

Adima, A ;

Bied, C ;

Moreau, JLJE ;

Man, MWC .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (12) :2582-2588

[2] THE SYNTHESIS OF OPTICALLY-ACTIVE THIAZOLINE AND THIAZOLE DERIVED PEPTIDES FROM N-PROTECTED ALPHA-AMINO-ACIDS [J].

BODEN, CDJ ;

PATTENDEN, G ;

YE, T .

SYNLETT, 1995, (05) :417-419

[3] STUDIES ON THE TOTAL SYNTHESIS OF BOUVARDIN AND DEOXYBOUVARDIN - CYCLIC HEXAPEPTIDE CYCLIZATION STUDIES AND PREPARATION OF KEY PARTIAL STRUCTURES [J].

BOGER, DL ;

YOHANNES, D .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (03) :487-499

[4] Facile syntheses of 3-halo and mixed 3,5-dihalo analogues of N-acetyl-L-tyrosine via sulfonic acid-catalysed regioselective monohalogenation [J].

Bovonsombat, Pakorn ;

Khanthapura, Pratheep ;

Krause, Michael M. ;

Leykajarakul, Juthamard .

TETRAHEDRON LETTERS, 2008, 49 (49) :7008-7011

[5] Marine cyanobacteria - a prolific source of natural products [J].

Burja, AM ;

Banaigs, B ;

Abou-Mansour, E ;

Burgess, JG ;

Wright, PC .

TETRAHEDRON, 2001, 57 (46) :9347-9377

[6]

CABRE J, 1984, SYNTHESIS-STUTTGART, P413

[7] EFFECT OF TERTIARY BASES ON O-BENZOTRIAZOLYLURONIUM SALT-INDUCED PEPTIDE SEGMENT COUPLING [J].

CARPINO, LA ;

EL-FAHAM, A .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (04) :695-698

[8] EFFICIENCY IN PEPTIDE COUPLING - 1-HYDROXY-7-AZABENZOTRIAZOLE VS 3,4-DIHYDRO-3-HYDROXY-4-OXO-1,2,3-BENZOTRIAZINE [J].

CARPINO, LA ;

EL-FAHAM, A ;

ALBERICIO, F .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (11) :3561-3564

[9] 1-HYDROXY-7-AZABENZOTRIAZOLE - AN EFFICIENT PEPTIDE COUPLING ADDITIVE [J].

CARPINO, LA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) :4397-4398

[10] Towards the stereochemical assignment of natural lydiamycin A [J].

Chen, Bo ;

Dai, Lu ;

Zhang, Hui ;

Tan, Wenfei ;

Xu, Zhengshuang ;

Ye, Tao .

CHEMICAL COMMUNICATIONS, 2010, 46 (04) :574-576

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