Stereoselective Total Synthesis of Unnatural (+)-Anisomycin

被引：9

作者：

Ajay, Sama ^{[1
]}

Saidhareddy, Puli ^{[1
]}

Shaw, Arun K. ^{[1
]}

机构：

[1] CSIR CDRI, Med & Proc Chem Div, Sect 10,Sitapur Rd, Lucknow 226031, UP, India

来源：

SYNTHESIS-STUTTGART | 2016年 / 48卷 / 08期

关键词：

anisomycin; D-glucose; total synthesis; Grignard reaction; chloromesyl chloride; azidation; cyclization; BIOLOGICAL EVALUATION; POLYHYDROXYLATED PYRROLIDINE; ANTIBIOTIC ANISOMYCIN; (-)-ANISOMYCIN; IMINOSUGARS; INHIBITORS; ANALOGS;

D O I：

10.1055/s-0035-1561365

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereoselective total synthesis of unnatural (+)-anisomycin from D-glucose has been achieved with an overall yield of 23%. The key synthetic features are regioselective opening of an epoxide, azidation of the resulting alcohol, and finally one-pot hydrogenation leading to cyclization to the pyrrolidine ring in a single step.

引用

页码：1191 / 1196

页数：6

共 39 条

[1]

[Anonymous], 2007, IMINOSUGARS SYNTHESI

[2]

ARMSTRONG T, 1955, ANTIBIOT ANNU, P824

[3] Design, synthesis and biological evaluation of bicyclic iminosugar hybrids: conformational constraint as an effective tool for tailoring the selectivity of α-glucosidase inhibitors [J].

Arora, Inderpreet ;

Kashyap, Vivek Kr ;

Singh, Alok Kumar ;

Dasgupta, Arunava ;

Kumar, Brijesh ;

Shaw, Arun K. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (35) :6855-6868

[4] ANISOMYCIN .I. DETERMINATION OF STRUCTURE AND STEREOCHEMISTRY OF ANISOMYCIN [J].

BEEREBOOM, JJ ;

BUTLER, K ;

PENNINGTON, FC ;

SOLOMONS, IA .

JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (07) :2334-+

[5] Highly diastereoselective additions to polyhydroxylated pyrrolidine cyclic imines: Ready elaboration of aza-sugar scaffolds to create diverse carbohydrate-processing enzyme probes [J].

Chapman, TM ;

Courtney, S ;

Hay, P ;

Davis, BG .

CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (14) :3397-3414

[6] Formal synthesis of (-) anisomycin via organocatalysis [J].

Chouthaiwale, Pandurang V. ;

Kotkar, Shriram P. ;

Sudalai, Arumugam .

ARKIVOC, 2009, :88-94

[7] Synthesis and enzyme inhibition study of unnatural saturated and unsaturated C-alkyl pyrrolidine iminosugars from D-mannose derived nitrone [J].

Das, Pintu ;

Kundooru, Somireddy ;

Pandole, Ravikant ;

Sharma, Sandeep K. ;

Singh, Bhupendra N. ;

Shaw, Arun K. .

TETRAHEDRON-ASYMMETRY, 2016, 27 (2-3) :101-106

[8] Enantioselective Copper-Catalysed Propargylic Substitution: Synthetic Scope Study and Application in Formal Total Syntheses of (+)-Anisomycin and (-)-Cytoxazone [J].

Detz, Remko J. ;

Abiri, Zohar ;

le Griel, Remi ;

Hiemstra, Henk ;

van Maarseveen, Jan H. .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (21) :5921-5930

[9]

FRYE WW, 1955, ANTIBIOT ANNU, P820

[10]

GROLLMAN AP, 1967, J BIOL CHEM, V242, P3226

← 1 2 3 4 →