IMINO DIELS-ALDER CYCLOADDITIONS - AN APPLICATION TO THE SYNTHESIS OF (+/-)-ARISTEROMYCIN

被引:37
作者
MAGGINI, M [1 ]
PRATO, M [1 ]
SCORRANO, G [1 ]
机构
[1] CNR, CTR MECCANISMI REAZ ORGAN, DIPARTIMENTO CHIM ORGAN, VIA MARZOLO 1, I-35131 PADUA, ITALY
关键词
D O I
10.1016/S0040-4039(00)97035-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A formal synthesis of (±)-aristeromycin starting from the imino Diels-Alder cycloadduct 3a has been achieved with high overall yield. A novel method for the in situ preparation of N-sulfonylimines is reported. © 1990.
引用
收藏
页码:6243 / 6246
页数:4
相关论文
共 25 条
[1]   HETEROCYCLEN DURCH DIENSYNTHESE .2. N-[BUTYLOXYCARBONYLMENTHYLEN]-P-TOLUOLSULFONAMID EIN NEUES DIENOPHIL ZUR DARSTELLUNG VON PYRIDIN- PIPERIDEIN- UND PIPERIDIN-DERIVATEN DURCH DIELS-ALDER-SYNTHESE [J].
ALBRECHT, R ;
KRESZE, G .
CHEMISCHE BERICHTE-RECUEIL, 1965, 98 (05) :1431-&
[2]   AN ENANTIOCONVERGENT ROUTE TO CARBOCYCLIC NUCLEOSIDES (-)-ARISTEROMYCIN AND (-)-NEPLANOCIN A VIA THE ASYMMETRIC DIELS-ALDER REACTION [J].
ARAI, Y ;
HAYASHI, Y ;
YAMAMOTO, M ;
TAKAYEMA, H ;
KOIZUMI, T .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (12) :3133-3140
[3]   ENANTIOSELECTIVE SYNTHESIS OF THE CARBOCYCLIC NUCLEOSIDES (-)-ARISTEROMYCIN AND (-)-NEPLANOCIN-A BY A CHEMICOENZYMATIC APPROACH [J].
ARITA, M ;
ADACHI, K ;
ITO, Y ;
SAWAI, H ;
OHNO, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (12) :4049-4055
[4]  
BARCO A, 1982, LIEBIGS ANN CHEM, P960
[5]  
BOGER DL, 1987, ORGANIC CHEM HETERO, V47, pCH2
[6]   (+/-) 4-BETA-AMINO-2-ALPHA,3-ALPHA-DIHYDROXY-1-BETA-CYCLOPENTANEMETHANOL HYDROCHLORIDE - CARBOCYCLIC RIBOFURANOSYLAMINE FOR THE SYNTHESIS OF CARBOCYCLIC NUCLEOSIDES [J].
CERMAK, RC ;
VINCE, R .
TETRAHEDRON LETTERS, 1981, 22 (25) :2331-2332
[7]   PALLADIUM-ASSISTED ROUTE TO CARBOCYCLIC NUCLEOSIDES - A FORMAL SYNTHESIS OF (+/-)-ARISTEROMYCIN [J].
DEARDORFF, DR ;
SHULMAN, MJ ;
SHEPPECK, JE .
TETRAHEDRON LETTERS, 1989, 30 (48) :6625-6628
[8]   A CONCISE APPROACH TO ENANTIOMERICALLY PURE CARBOCYCLIC RIBOSE ANALOGS - SYNTHESIS OF (4S,5R,6R,7R)-7-(HYDROXYMETHYL)SPIRO[2.4]HEPTANE-4,5,6-TRIOL 7-O-(DIHYDROGEN PHOSPHATE) [J].
GAUDINO, JJ ;
WILCOX, CS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) :4374-4380
[9]  
HELMCHEN G, 1986, MODERN SYNTHETIC MET, V4, P262
[10]   NUCLEIC-ACID COMPONENTS AND THEIR ANALOGS .181. PREPARATION OF SUBSTITUTED (+ OR -)-5TERT-HYDROXYMETHYL-3TERT-AMINOCYCLOPENTANE-1R,2C-DIOL DERIVATIVES RELATED TO CARBOCYCLIC RIBONUCLEOSIDE ANALOGS [J].
HOLY, A .
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1976, 41 (02) :647-665