Formal synthesis of (-) anisomycin via organocatalysis

被引:13
作者
Chouthaiwale, Pandurang V. [1 ]
Kotkar, Shriram P. [1 ]
Sudalai, Arumugam [1 ]
机构
[1] Natl Chem Lab, Chem Engn & Proc Dev Div, Pashan Rd, Pune 411008, Maharashtra, India
关键词
alpha-amination; alpha-aminoxylation; anisomycin; olefination; proline; STEREOSELECTIVE NUCLEOPHILIC-SUBSTITUTION; ENANTIOSELECTIVE SYNTHESIS; (-)-ANISOMYCIN; OLEFINATION; ALDEHYDES;
D O I
10.3998/ark.5550190.0010.210
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient formal synthesis of (-) anisomycin (1), a potent antibiotic agent, has been achieved in good yields and excellent diastereoselectivity. The key steps are proline-catalyzed sequential alpha-amination or alpha-aminoxylation of aldehyde 2 followed by tandem Horner-Wadsworth-Emmons olefination.
引用
收藏
页码:88 / 94
页数:7
相关论文
共 30 条
[1]   A NITRONE-BASED APPROACH TO THE ENANTIOSELECTIVE TOTAL SYNTHESIS OF (-)-ANISOMYCIN [J].
BALLINI, R ;
MARCANTONI, E ;
PETRINI, M .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (04) :1316-1318
[2]  
Chandrasekhar S, 2002, SYNTHESIS-STUTTGART, P1867
[3]  
Chang MY, 2003, HETEROCYCLES, V60, P1203
[4]   Formal total synthesis of enantiopure (-)-anisomycin, antibiotic from Streptomyces [J].
Delair, P ;
Brot, E ;
Kanazawa, A ;
Greene, AE .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (04) :1383-1386
[5]  
FRYE WW, 1955, ANTIBIOT ANNU, P820
[6]  
GROLLMAN AP, 1967, J BIOL CHEM, V242, P3226
[7]   Exploratory synthetic studies of the alpha-methoxylation of amides via cuprous ion-promoted decomposition of o-diazobenzamides [J].
Han, G ;
LaPorte, MG ;
McIntosh, MC ;
Weinreb, SM ;
Parvez, M .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9483-9493
[8]   Microwave-assisted rearrangement of vinylaziridines to 3-pyrrolines: Formal synthesis of (-)-anisomycin [J].
Hirner, S ;
Somfai, P .
SYNLETT, 2005, (20) :3099-3102
[9]   An improved formal total synthesis of (-)-anisomycin [J].
Huang, PQ ;
Zheng, X .
ARKIVOC, 2003, :7-14
[10]   An aldol-based approach to the synthesis of the antibiotic Anisomycin [J].
Hulme, AN ;
Rosser, EM .
ORGANIC LETTERS, 2002, 4 (02) :265-267