A stereodivergent synthesis of virantmycin by an enzyme-mediated diester desymmetrization and a highly hindered aryl amination

被引：30

作者：

Back, TG ^{[1
]}

Wulff, JE ^{[1
]}

机构：

[1] Univ Calgary, Dept Chem, Calgary, AB T2N 1N4, Canada

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 47期

关键词：

aryl amination; enzyme catalysis; esterases; natural products; total synthesis;

D O I：

10.1002/anie.200461327

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical equation presented). Both enantiomers of the antiviral agent virantmycin were synthesized in a sequence of reactions in which the key steps were a highly stereoselective porcine liver esterase(PLE) mediated desymmetrization of a prochiral diester and a remarkably effective intramolecular aryl amination of an ortho-substituted aryl bromide with a highly hindered α-quaternary formamide (see retrosynthetic scheme).

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页码：6493 / 6496

页数：4

相关论文

共 36 条

[1] Synthesis, resolution, and application of 2,2′-bis(diphenylphosphino)-3,3′-binaphtho[b]furan (BINAPFu) [J].

Andersen, NG ;

Parvez, M ;

McDonald, R ;

Keay, BA .

CANADIAN JOURNAL OF CHEMISTRY, 2004, 82 (02) :145-161

[2] 2-furyl phosphines as ligands for transition-metal-mediated organic synthesis [J].

Andersen, NG ;

Keay, BA .

CHEMICAL REVIEWS, 2001, 101 (04) :997-1030

[3]

[Anonymous], 2002, HDB ORGANOPALLADIUM

[4] Additions of organocopper reagents and heteroatom nucleophiles to 1-phenylseleno-2-(p-toluenesulfonyl)ethyne.: Preparation of vinyl and allenic sulfones and formation of Michael, anti-Michael, and rearrangement products [J].

Back, TG ;

Bethell, RJ ;

Parvez, M ;

Wehrli, D .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22) :7908-7919

[5] ENZYME CATALYZED-HYDROLYSIS OF DIALKYLATED PROPANEDIOIC ACID DIESTERS, CHAIN-LENGTH DEPENDENT REVERSAL OF ENANTIOSELECTIVITY [J].

BJORKLING, F ;

BOUTELJE, J ;

GATENBECK, S ;

HULT, K ;

NORIN, T ;

SZMULIK, P .

TETRAHEDRON, 1985, 41 (07) :1347-1352

[6] A flexible synthesis of indoline, indolizidine, and pyrrolizidine derivatives [J].

Bytschkov, I ;

Siebeneicher, H ;

Doye, S .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (15) :2888-2902

[7]

DAVIES HG, 1989, BIOTRANSFORMATIONS P, pCH2

[8] GRIGNARD ADDITION-REACTIONS TO 1,4-DIFUNCTIONALIZED BUT-2-YNES [J].

DESILVA, AN ;

FRANCIS, CL ;

WARD, AD .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1993, 46 (11) :1657-1671

[9] A second-generation catalyst for aryl halide amination: Mixed secondary amines from aryl halides and primary amines catalyzed by (DPPF)PdCl2 [J].

Driver, MS ;

Hartwig, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (30) :7217-7218

[10] Amination reactions of aryl halides with nitrogen-containing reagents mediated by palladium/imidazolium salt systems [J].

Grasa, GA ;

Viciu, MS ;

Huang, JK ;

Nolan, SP .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (23) :7729-7737

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