HIGHLY EFFECTIVE AND PRACTICAL ENANTIOSELECTIVE SYNTHESIS OF HALF-ESTERS OF BICYCLO[2.2.1]HEPTANEDICARBOXYLIC ACID

被引:36
作者
OHTANI, M
MATSUURA, T
WATANABE, F
NARISADA, M
机构
[1] Shionogi Research Laboratories, Shionogi & Co., Ltd., Fukushima-ku
关键词
D O I
10.1021/jo00013a009
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An effective and practical enantioselective synthesis of half-esters of bicyclo[2.2.1]heptane-2,3-dicarboxylic acid was developed by enantioselective fission of sigma-symmetrical cyclic anhydrides with chiral mandelic acid derivatives, followed by deprotection of the mandelate moiety, crystallization, and further modification. These half-esters are very attractive chiral building blocks for numerous natural products, and this new method makes possible their synthesis via common intermediates with high optical purity.
引用
收藏
页码:4120 / 4123
页数:4
相关论文
共 25 条
  • [1] PREPARATION OF METHYL 10-OXO-15S-HYDROXYPROSTA-5E,13Z-DIENOATE
    ARNDT, HC
    RAJANI, C
    [J]. TETRAHEDRON LETTERS, 1982, 23 (23) : 2365 - 2368
  • [2] A SIMPLE SYNTHESIS OF A STABLE THROMBOXANE-A2 ANALOG
    BARRACLOUGH, P
    [J]. TETRAHEDRON LETTERS, 1980, 21 (19) : 1897 - 1900
  • [3] STEREOSELECTIVE PIG-LIVER ESTERASE-CATALYZED HYDROLYSIS OF RIGID BICYCLIC MESO-DIESTERS - PREPARATION OF OPTICALLY PURE 4,7-EPOXYTETRA-HYDROPHTHALIDES AND HEXA-HYDROPHTHALIDES
    BLOCH, R
    GUIBEJAMPEL, E
    GIRARD, C
    [J]. TETRAHEDRON LETTERS, 1985, 26 (34) : 4087 - 4090
  • [4] NOVEL SYNTHESIS OF 5-MEMBERED AND 6-MEMBERED SPIRO GAMMA-LACTONES IN RIGID BICYCLIC SYSTEMS
    CANONNE, P
    BELANGER, D
    LEMAY, G
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (20) : 3953 - 3959
  • [5] SYNTHESIS OF CARBOCYCLIC C-NUCLEOSIDE ANALOGS FROM 8,9,10-TRINORBORN-5-EN-2-OL
    COOKSON, RC
    DUDFIELD, PJ
    SCOPES, DIC
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (03): : 393 - 398
  • [6] ASYMMETRIC DIELS-ALDER REACTION - COOPERATIVE BLOCKING EFFECT IN ORGANIC-SYNTHESIS
    FURUTA, K
    IWANAGA, K
    YAMAMOTO, H
    [J]. TETRAHEDRON LETTERS, 1986, 27 (37) : 4507 - 4510
  • [7] ASYMMETRIC DIELS-ALDER REACTION - A FACILE ROUTE TO CHIRAL ALKYL HYDROGEN CYCLOHEXENE-1,2-DICARBOXYLATE
    FURUTA, K
    HAYASHI, S
    MIWA, Y
    YAMAMOTO, H
    [J]. TETRAHEDRON LETTERS, 1987, 28 (47) : 5841 - 5844
  • [8] THE SYNTHESIS OF POTENT THROMBOXANE-A2/PROSTAGLANDIN ENDOPEROXIDE RECEPTOR ANTAGONIST
    HAMANAKA, N
    SEKO, T
    MIYAZAKI, T
    NAKA, M
    FURUTA, K
    YAMAMOTO, H
    [J]. TETRAHEDRON LETTERS, 1989, 30 (18) : 2399 - 2402
  • [9] HIGH STEREOSELECTIVITY IN LEWIS-ACID-CATALYZED AND UNCATALYZED DIELS-ALDER REACTIONS OF THE FUMARATE OF (S)-ETHYL LACTATE
    HARTMANN, H
    HADY, AFA
    SARTOR, K
    WEETMAN, J
    HELMCHEN, G
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (11): : 1143 - 1145
  • [10] HELMCHEN G, 1986, MODERN SYNTHETIC MET, V4, P262