A NOVEL SYNTHESIS OF THE (2R,3S)-3-AMINO-2-HYDROXYCARBOXYLIC AND (2S,3R)-3-AMINO-2-HYDROXYCARBOXYLIC ACID-DERIVATIVES, THE KEY COMPONENTS OF A RENIN INHIBITOR AND BESTATIN, FROM METHYL (R)-MANDELATE AND (S)-MANDELATE

被引:62
作者
KOBAYASHI, Y [1 ]
TAKEMOTO, Y [1 ]
ITO, Y [1 ]
TERASHIMA, S [1 ]
机构
[1] SAGAMI CHEM RES CTR,NISHI OHNUMA,SAGAMIHARA,KANAGAWA 229,JAPAN
关键词
D O I
10.1016/S0040-4039(00)89018-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The title synthesis could be accomplished by featuring the [2+2]-cycloaddition reaction of a chiral imine with benzyloxyketene, alcoholysis of the formed 2-azetidinone derivative, and reductive removal of the mandelate-derived benzylic oxygen by way of a 2-oxazolidone derivative. © 1990.
引用
收藏
页码:3031 / 3034
页数:4
相关论文
共 13 条
  • [1] HARADA H, 1989, CHEM PHARM BULL, V37, P2570
  • [2] Holden K. G., 1982, CHEM BIOL BETA LACTA, V2, P114
  • [3] AN ENANTIOSELECTIVE BETA-LACTAM SYNTHESIS STARTING FROM L-(S)-GLYCERALDEHYDE ACETONIDE
    HUBSCHWERLEN, C
    SCHMID, G
    [J]. HELVETICA CHIMICA ACTA, 1983, 66 (07) : 2206 - 2209
  • [4] DESIGN AND SYNTHESIS OF AN ORALLY POTENT HUMAN RENIN INHIBITOR CONTAINING A NOVEL AMINO-ACID, CYCLOHEXYLNORSTATINE
    IIZUKA, K
    KAMIJO, T
    HARADA, H
    AKAHANE, K
    KUBOTA, T
    UMEYAMA, H
    KISO, Y
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (21) : 1678 - 1680
  • [5] IIZUKA K, 1987, Patent No. 62234071
  • [6] ITO Y, 1990, HETEROCYCLES, V30, P299
  • [7] NOVEL SYNTHESES OF THE CARBAPENEM KEY INTERMEDIATES, (3R,4R)-4-ACETOXY-3-[(R)-1-(TERT-BUTYLDIMETHYLSILYLOXY)ETHYL]-2-AZETIDINONE AND (3S,4R)-3-[(R)-1-(TERT-BUTYLDIMETHYLSILYLOXY)ETHYL]-4-CARBOXYMETHYL-2-AZETIDINONE, FROM (S)-ETHYL LACTATE
    ITO, Y
    KOBAYASHI, Y
    KAWABATA, T
    TAKASE, M
    TERASHIMA, S
    [J]. TETRAHEDRON, 1989, 45 (18) : 5767 - 5790
  • [8] KAMIJO T, 1989, Patent No. 1172365
  • [9] MATSUDA F, UNPUB CHEM LETT
  • [10] A FACILE SYNTHESIS OF BESTATIN
    NISHIZAWA, R
    SAINO, T
    SUZUKI, M
    FUJII, T
    SHIRAI, T
    AOYAGI, T
    UMEZAWA, H
    [J]. JOURNAL OF ANTIBIOTICS, 1983, 36 (06) : 695 - 699