A Lanthanide(III) Triflate Mediated Macrolactonization/Solid-Phase Synthesis Approach for Depsipeptide Synthesis

被引：21

作者：

Goodreid, Jordan D. ^{[1
]}

dos Santos, Eduardo da Silveira ^{[1
]}

Batey, Robert A. ^{[1
]}

机构：

[1] Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 09期

基金：

加拿大自然科学与工程研究理事会; 加拿大健康研究院;

关键词：

ANTIMICROBIAL CYCLIC DEPSIPEPTIDE; ACTIVE ACYLATION CATALYST; MEDICINAL CHEMISTRY; CEPHALOSPOROLIDE D; LEWIS-ACID; ANTIBIOTICS; ANHYDRIDE; PHOSPHATE; ACYLDEPSIPEPTIDES; STEREOCHEMISTRY;

D O I：

10.1021/acs.orglett.5b00781

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The effect of dysprosium(III) triflate on macrolactonization reactions to form depsipeptides using MNBA (Shiina's reagent) is reported. Improved yields were obtained for the formation of 16-membered depsipeptides using lanthanide triflate additives. The use of a macrocyclization strategy permits the use of a semiautomated solid-phase synthesis approach for the rapid synthesis of analogues of the antibacterial A54556 acyldepsipeptides in only two physical operations, requiring only final product purification after cyclization.

引用

页码：2182 / 2185

页数：4

共 37 条

[1] Marine natural products [J].

Blunt, John W. ;

Copp, Brent R. ;

Munro, Murray H. G. ;

Northcote, Peter T. ;

Prinsep, Michele R. .

NATURAL PRODUCT REPORTS, 2010, 27 (02) :165-237

[2] Dysregulation of bacterial proteolytic machinery by a new class of antibiotics [J].

Brötz-Oesterhelt, H ;

Beyer, D ;

Kroll, HP ;

Endermann, R ;

Ladel, C ;

Schroeder, W ;

Hinzen, B ;

Raddatz, S ;

Paulsen, H ;

Henninger, K ;

Bandow, JE ;

Sahl, HG ;

Labischinski, H .

NATURE MEDICINE, 2005, 11 (10) :1082-1087

[3] Biomimetic monoacylation of diols in water. Lanthanide-promoted reactions of methyl benzoyl phosphate [J].

Cameron, LL ;

Wang, SC ;

Kluger, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (34) :10721-10726

[4] Restriction of the Conformational Dynamics of the Cyclic Acyldepsipeptide Antibiotics Improves Their Antibacterial Activity [J].

Carney, Daniel W. ;

Schmitz, Karl R. ;

Truong, Jonathan V. ;

Sauer, Robert T. ;

Sello, Jason K. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (05) :1922-1929

[5] A one-step procedure for the monoacylation of symmetrical 1,2-diols [J].

Clarke, PA ;

Kayaleh, NE ;

Smith, MA ;

Baker, JR ;

Bird, SJ ;

Chan, C .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (15) :5226-5231

[6] Selective mono-acylation of meso- and C2-symmetric 1,3-and 1,4-diols [J].

Clarke, PA .

TETRAHEDRON LETTERS, 2002, 43 (27) :4761-4763

[7] A macrolactonization approach to the total synthesis of the antimicrobial cyclic depsipeptide LI-F04a and diastereoisomeric analogues [J].

Cochrane, James R. ;

Yoon, Dong Hee ;

McErlean, Christopher S. P. ;

Jolliffe, Katrina A. .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2012, 8 :1344-1351

[8] Total Synthesis and Assignment of the Side Chain Stereochemistry of LI-F04a: An Antimicrobial Cyclic Depsipeptide [J].

Cochrane, James R. ;

McErlean, Christopher S. P. ;

Jolliffe, Katrina A. .

ORGANIC LETTERS, 2010, 12 (15) :3394-3397

[9] Highly efficient and versatile acetylation of alcohols catalyzed by cerium(III) triflate [J].

Dalpozzo, R ;

De Nino, A ;

Maiuolo, L ;

Procopio, A ;

Nardi, M ;

Bartoli, G ;

Romeo, R .

TETRAHEDRON LETTERS, 2003, 44 (30) :5621-5624

[10] Erbium(III) chloride: a very active acylation catalyst [J].

Dalpozzo, Renato ;

De Nino, Antonio ;

Maiuolo, Loredana ;

Oliverio, Manuela ;

Procopio, Antonio ;

Russo, Beatrice ;

Tocci, Amedeo .

AUSTRALIAN JOURNAL OF CHEMISTRY, 2007, 60 (01) :75-79

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