AN EFFICIENT AND DIASTEREOSELECTIVE [2+2] CYCLOADDITION - CONVENIENT AND ENANTIOSELECTIVE ROUTE TO TRANS-2',3'-DIHYDROXYMETHYLCYCLOBUTANE NUCLEOSIDE ANALOGS

被引:44
作者
AHMAD, S
机构
关键词
D O I
10.1016/0040-4039(91)85023-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient route to (2S-trans)-2,3-bis[(benzoyloxy)methyl]cyclobutanone (3a), a key intermediate in the synthesis of cyclobutane nucleoside analogs, via a novel asymmetric [2 + 2] cycloaddition, is described.
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页码:6997 / 7000
页数:4
相关论文
共 19 条
[1]   CYCLOBUTANONES AND CYCLOBUTENONES IN NATURE AND IN SYNTHESIS [J].
BELLUS, D ;
ERNST, B .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (06) :797-827
[2]   SYNTHESIS AND ANTIVIRAL ACTIVITY OF ENANTIOMERIC FORMS OF CYCLOBUTYL NUCLEOSIDE ANALOGS [J].
BISACCHI, GS ;
BRAITMAN, A ;
CIANCI, CW ;
CLARK, JM ;
FIELD, AK ;
HAGEN, ME ;
HOCKSTEIN, DR ;
MALLEY, MF ;
MITT, T ;
SLUSARCHYK, WA ;
SUNDEEN, JE ;
TERRY, BJ ;
TUOMARI, AV ;
WEAVER, ER ;
YOUNG, MG ;
ZAHLER, R .
JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (04) :1415-1421
[3]   ENANTIOSELECTIVE TOTAL SYNTHESIS OF BILOBALIDE, A C15 GINKGOLIDE [J].
COREY, EJ ;
SU, WG .
TETRAHEDRON LETTERS, 1988, 29 (28) :3423-3426
[4]   (+/-)-(1-ALPHA,2-BETA,3-ALPHA)-9-[2,3-BIS(HYDROXYMETHYL)-CYCLOBUTYL]GUANINE [(+/-)-BHCG OR SQ 33054] - A POTENT AND SELECTIVE INHIBITOR OF HERPESVIRUSES [J].
FIELD, AK ;
TUOMARI, AV ;
MCGEEVERRUBIN, B ;
TERRY, BJ ;
MAZINA, KE ;
HAFFEY, ML ;
HAGEN, ME ;
CLARK, JM ;
BRAITMAN, A ;
SLUSARCHYK, WA ;
YOUNG, MG ;
ZAHLER, R .
ANTIVIRAL RESEARCH, 1990, 13 (01) :41-52
[5]   ASYMMETRIC DIELS-ALDER REACTION - COOPERATIVE BLOCKING EFFECT IN ORGANIC-SYNTHESIS [J].
FURUTA, K ;
IWANAGA, K ;
YAMAMOTO, H .
TETRAHEDRON LETTERS, 1986, 27 (37) :4507-4510
[6]   ASYMMETRIC DIELS-ALDER REACTION - A FACILE ROUTE TO CHIRAL ALKYL HYDROGEN CYCLOHEXENE-1,2-DICARBOXYLATE [J].
FURUTA, K ;
HAYASHI, S ;
MIWA, Y ;
YAMAMOTO, H .
TETRAHEDRON LETTERS, 1987, 28 (47) :5841-5844
[7]   HIGH STEREOSELECTIVITY IN LEWIS-ACID-CATALYZED AND UNCATALYZED DIELS-ALDER REACTIONS OF THE FUMARATE OF (S)-ETHYL LACTATE [J].
HARTMANN, H ;
HADY, AFA ;
SARTOR, K ;
WEETMAN, J ;
HELMCHEN, G .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (11) :1143-1145
[8]   ASYMMETRIC [2+2] CYCLO-ADDITION REACTION CATALYZED BY A CHIRAL TITANIUM REAGENT [J].
HAYASHI, Y ;
NARASAKA, K .
CHEMISTRY LETTERS, 1989, (05) :793-796
[9]  
HONJO M, 1989, CHEM PHARM BULL, V37, P1413
[10]   EFFICIENT SYNTHESES OF PROTECTED (2S,3S)-2,3-BIS(HYDROXYMETHYL)CYCLOBUTANONE, KEY INTERMEDIATES FOR THE SYNTHESIS OF CHIRAL CARBOCYCLIC ANALOGS OF OXETANOCIN [J].
HSIAO, CN ;
HANNICK, SM .
TETRAHEDRON LETTERS, 1990, 31 (46) :6609-6612