Total Synthesis of Desmethyl Macrolide Antibiotics

被引：13

作者：

Andrade, Rodrigo B. ^{[1
]}

机构：

[1] Temple Univ, Dept Chem, Philadelphia, PA 19122 USA

来源：

SYNLETT | 2015年 / 26卷 / 16期

基金：

美国国家卫生研究院;

关键词：

total synthesis; desmethyl macrolides; ketolide antibiotics; telithromycin; erythromycin; OLEFIN METATHESIS CATALYSTS; PEPTIDYL TRANSFERASE CENTER; ANTIBACTERIAL ACTIVITY; SECONDARY ALCOHOLS; HIGHLY POTENT; ERYTHROMYCIN; RESISTANT; KETOLIDES; STEREOCHEMISTRY; TELITHROMYCIN;

D O I：

10.1055/s-0034-1381047

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Macrolide antibiotics occupy a special place in the history of organic chemistry and medicine. This account chronicles the evolution of our approach that ultimately led to the successful total syntheses of four desmethyl (i.e., Me -> H) analogues of telithromycin, a semisynthetic derivative of the flagship macrolide antibiotic, erythromycin. 1 Introduction 2 Project Rationale and Retrosynthetic Analysis 3 Lessons Learned from the Total Synthesis of 4,8,10-Tridesmethyl Telithromycin 4 Total Synthesis of 4,10-Didesmethyl Telithromycin 5 Total Synthesis of 4,8-Didesmethyl Telithromycin 6 Total Synthesis of 4-Desmethyl Telithromycin 7 Biological Evaluation of Desmethyl Telithromycin Analogues 8 Concluding Remarks

引用

页码：2199 / 2215

页数：17

共 52 条

[11] Synthesis and antibacterial activity of HMR 3647 a new ketolide highly potent against erythromycin-resistant and susceptible pathogens [J].

Denis, A ;

Agouridas, C ;

Auger, JM ;

Benedetti, Y ;

Bonnefoy, A ;

Bretin, F ;

Chantot, JF ;

Dussarat, A ;

Fromentin, C ;

D'Ambrières, SG ;

Lachaud, S ;

Laurin, P ;

Le Martret, O ;

Loyau, V ;

Tessot, N ;

Pejac, JM ;

Perron, S .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (21) :3075-3080

[12] READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156

[13] Structures of the Escherichia coli ribosome with antibiotics bound near the peptidyl transferase center explain spectra of drug action [J].

Dunkle, Jack A. ;

Xiong, Liqun ;

Mankin, Alexander S. ;

Cate, Jamie H. D. .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2010, 107 (40) :17152-17157

[14] MILD ALCOHOL METHYLATION PROCEDURES FOR THE SYNTHESIS OF POLYOXYGENATED NATURAL-PRODUCTS - APPLICATIONS TO THE SYNTHESIS OF LONOMYCIN-A [J].

EVANS, DA ;

RATZ, AM ;

HUFF, BE ;

SHEPPARD, GS .

TETRAHEDRON LETTERS, 1994, 35 (39) :7171-7172

[15] ENANTIOSELECTIVE ALDOL CONDENSATIONS .2. ERYTHRO-SELECTIVE CHIRAL ALOL CONDENSATIONS VIA BORON ENOLATES [J].

EVANS, DA ;

BARTROLI, J ;

SHIH, TL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (08) :2127-2129

[16] Desmethyl Macrolides: Synthesis and Evaluation of 4-Desmethyl Telithromycin [J].

Glassford, Ian ;

Lee, Miseon ;

Wagh, Bharat ;

Velyadapu, Venkata ;

Paul, Tapas ;

Sandelin, Gary ;

DeBrosse, Charles ;

Klepacki, Dorota ;

Small, Meagan C. ;

MacKerell, Alexander D., Jr. ;

Andrade, Rodrigo B. .

ACS MEDICINAL CHEMISTRY LETTERS, 2014, 5 (09) :1021-1026

[17] An abiotic strategy for the enantioselective synthesis of erythromycin B [J].

Hergenrother, PJ ;

Hodgson, A ;

Judd, AS ;

Lee, WC ;

Martin, SF .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (28) :3278-3281

[18] RAPID ESTERIFICATION BY MEANS OF MIXED ANHYDRIDE AND ITS APPLICATION TO LARGE-RING LACTONIZATION [J].

INANAGA, J ;

HIRATA, K ;

SAEKI, H ;

KATSUKI, T ;

YAMAGUCHI, M .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1979, 52 (07) :1989-1993

[19] Precursor-directed biosynthesis of erythromycin analogs by an engineered polyketide synthase [J].

Jacobsen, JR ;

Hutchinson, CR ;

Cane, DE ;

Khosla, C .

SCIENCE, 1997, 277 (5324) :367-369

[20] CATALYTIC EFFECT OF NICKEL(II) CHLORIDE AND PALLADIUM(II) ACETATE ON CHROMIUM(II)-MEDIATED COUPLING REACTION OF IODO OLEFINS WITH ALDEHYDES [J].

JIN, H ;

UENISHI, J ;

CHRIST, WJ ;

KISHI, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (18) :5644-5646

← 1 2 3 4 5 6 →