PI-ALLYL PALLADIUM RING-CLOSURE STRATEGY FOR THE SYNTHESIS OF A 1-BETA-METHYLCARBAPENEM INTERMEDIATE

被引:21
作者
ROLAND, S
DURAND, JO
SAVIGNAC, M
GENET, JP
JUNG, F
机构
[1] ECOLE NATL SUPER CHIM,SYNTH ORGAN LAB,CNRS,URA 1381,F-75231 PARIS,FRANCE
[2] ZENECA PHARMA,CTR RECH,F-51064 REIMS,FRANCE
关键词
PALLADIUM CATALYST; CYCLIZATION; 1-METHYLENECARBAPENEM;
D O I
10.1016/0040-4039(95)00448-L
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new ring closure by pi-allyl palladium methodology is utilized in the synthesis of a 1-beta-methyl carbapenem intermediate from 2-acetoxy azetidinone in six steps (40% yield).
引用
收藏
页码:3007 / 3010
页数:4
相关论文
共 18 条
  • [1] STRUCTURE AND ABSOLUTE-CONFIGURATION OF THIENAMYCIN
    ALBERSSCHONBERG, G
    ARISON, BH
    HENSENS, OD
    HIRSHFIELD, J
    HOOGSTEEN, K
    KACZKA, EA
    RHODES, RE
    KAHAN, JS
    KAHAN, FM
    RATCLIFFE, RW
    WALTON, E
    RUSWINKLE, LJ
    MORIN, RB
    CHRISTENSEN, BG
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (20) : 6491 - 6499
  • [2] APPLICATIONS OF ORGANOMETALLIC REAGENTS IN BETA-LACTAM CHEMISTRY
    BARRETT, AGM
    STURGESS, MA
    [J]. TETRAHEDRON, 1988, 44 (18) : 5615 - 5652
  • [3] BATTISTINI C, 1984, TETRAHEDRON LETT, V24, P2395
  • [4] A NOVEL RING-CLOSURE STRATEGY FOR THE CARBAPENEMS - THE TOTAL SYNTHESIS OF (+)-THIENAMYCIN
    HANESSIAN, S
    DESILETS, D
    BENNANI, YL
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (10) : 3098 - 3103
  • [5] A NEW SYNTHETIC STRATEGY FOR THE PENEMS - TOTAL SYNTHESIS OF (5R,6S,8R)-6-(ALPHA-HYDROXYETHYL)-2-(HYDROXYMETHYL)PENEM-3-CARBOXYLIC ACID
    HANESSIAN, S
    BEDESCHI, A
    BATTISTINI, C
    MONGELLI, N
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (05) : 1438 - 1439
  • [6] ASYMMETRIC-SYNTHESIS OF BETA-LACTAMS AND THE CARBAPENEM ANTIBIOTIC (+)-PS-5
    HART, DJ
    LEE, CS
    PIRKLE, WH
    HYON, MH
    TSIPOURAS, A
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (19) : 6054 - 6056
  • [7] TOTAL SYNTHESIS OF (+/-)-THIENAMYCIN
    JOHNSTON, DBR
    SCHMITT, SM
    BOUFFARD, FA
    CHRISTENSEN, BG
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (01) : 313 - 315
  • [8] KAHAN FM, 1983, J ANTIMICROB CHEM S1, V12
  • [9] KAHAN JS, 1979, J ANTIBIOT, V32, P1
  • [10] STEREOSELECTIVE SYNTHESIS OF 1-BETA-METHYLCARBAPENEM
    KIM, CU
    LUH, B
    PARTYKA, RA
    [J]. TETRAHEDRON LETTERS, 1987, 28 (05) : 507 - 510