An efficient lactamization of fimbrolides to novel 1,5-dihydropyrrol-2-ones

被引：40

作者：

Goh, Wai Kean ^{[1
]}

Iskander, George ^{[1
]}

Black, David StC ^{[1
]}

Kumar, Naresh ^{[1
]}

机构：

[1] Univ New S Wales, Sch Chem, Sydney, NSW 2052, Australia

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 13期

基金：

澳大利亚研究理事会;

关键词：

D O I：

10.1016/j.tetlet.2007.01.165

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new versatile method for the conversion of fimbrolides to the corresponding novel dihydropyrrol-2-ones is described. This new efficient lactamization protocol has the advantage of higher yields and can be used for the synthesis of a series of new dihydropyrrol-2-ones with interesting anti-bacterial properties. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：2287 / 2290

页数：4

共 12 条

[1] Structural identification of a bacterial quorum-sensing signal containing boron [J].

Chen, X ;

Schauder, S ;

Potier, N ;

Van Dorsselaer, A ;

Pelczer, I ;

Bassler, BL ;

Hughson, FM .

NATURE, 2002, 415 (6871) :545-549

[2]

Egorova A. Y., 2001, CHEM HETEROCYCL COMP, V37, P694

[3] Small molecule inhibitors of bacterial quorum sensing and biofilm formation [J].

Geske, GD ;

Wezeman, RJ ;

Siegel, AP ;

Blackwell, HE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (37) :12762-12763

[4] Synthesis of 5-methoxylated 3-pyrrolin-2-ones via the rearrangement of chlorinated pyrrolidin-2-ones [J].

Ghelfi, F ;

Stevens, CV ;

Laureyn, I ;

Van Meenen, E ;

Rogge, TM ;

De Buyck, L ;

Nikitin, KV ;

Grandi, R ;

Libertini, E ;

Pagnoni, UM ;

Schenetti, L .

TETRAHEDRON, 2003, 59 (08) :1147-1157

[5] Inhibition of quorum sensing in Pseudomonas aeruginosa biofilm bacteria by a halogenated furanone compound [J].

Hentzer, M ;

Riedel, K ;

Rasmussen, TB ;

Heydorn, A ;

Andersen, JB ;

Parsek, MR ;

Rice, SA ;

Eberl, L ;

Molin, S ;

Hoiby, N ;

Kjelleberg, S ;

Givskov, M .

MICROBIOLOGY-SGM, 2002, 148 :87-102

[6]

KAZLAUSKAS R, 1977, TETRAHEDRON LETT, P37

[7] Study on halolactamization-γ-hydroxylation or haloiminolactonization of 2,3-alkadienamides [J].

Ma, SM ;

Me, HX .

TETRAHEDRON, 2005, 61 (01) :251-258

[8] Evidence that halogenated furanones from Delisea pulchra inhibit acylated homoserine lactone (AHL)-mediated gene expression by displacing the AHL signal from its receptor protein [J].

Manefield, M ;

de Nys, R ;

Kumar, N ;

Read, R ;

Givskov, M ;

Steinberg, P ;

Kjelleberg, SA .

MICROBIOLOGY-SGM, 1999, 145 :283-291

[9] Reinvestigation of the sulfuric acid-catalysed cyclisation of brominated 2-alkyllevulinic acids to 3-alkyl-5-methylene-2(5H)-furanones [J].

Manny, AJ ;

Kjelleberg, S ;

Kumar, N ;

deNys, R ;

Read, RW ;

Steinberg, P .

TETRAHEDRON, 1997, 53 (46) :15813-15826

[10] First synthesis of (R)-(-)-5-hydroxy-3-methyl-3-pyrrolin-2-one (jatropham) by lipase-catalyzed kinetic resolution [J].

Mase, N ;

Nishi, T ;

Takamori, Y ;

Yoda, H ;

Takabe, K .

TETRAHEDRON-ASYMMETRY, 1999, 10 (23) :4469-4471

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