Synthesis of vinca alkaloids and related compounds, LXXXVII. Reversed enantioselectivity in different approaches

被引:0
|
作者
Szabo, L [1 ]
Nagy, T [1 ]
Kalaus, G [1 ]
Szantay, C [1 ]
机构
[1] Tech Univ Budapest, Inst Organ Chem, H-1521 Budapest, Hungary
来源
ACH-MODELS IN CHEMISTRY | 1998年 / 135卷 / 04期
关键词
D O I
暂无
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Using the same chiral auxiliaries during the enantioselective synthesis of vincamine the absolute configuration depends on the selected approach. Starting from Wenkert enamine the natural (+)-vincamine, while using the reaction sequence through vincadifformine type intermediate, the (-)-enantiomer is formed.
引用
收藏
页码:641 / 651
页数:11
相关论文
共 50 条
  • [1] SYNTHESIS OF COMPOUNDS RELATED TO VINCA ALKALOIDS - STEREOSELECTIVE SYNTHESIS OF (+/-) HOMOEBURNAMINE
    BUZAS, A
    RETOURNE, C
    JACQUET, JP
    LAVIELLE, G
    TETRAHEDRON, 1978, 34 (19) : 3001 - 3004
  • [2] Synthesis of vinca alkaloids and related compounds, XCI. Synthesis of isolarutensine
    Lukacs, A
    Szabo, L
    Baitz-Gacs, E
    Dobo, A
    Kalaus, G
    Szantay, C
    HETEROCYCLES, 1998, 48 (02) : 249 - 257
  • [3] Synthesis of vinca alkaloids and related compounds .84. Sulfonamide derivatives of some vinca alkaloids with cardiovascular activity
    Moldvai, I
    TemesvariMajor, E
    Szantay, C
    Toth, G
    Karpati, E
    Szantay, C
    ARCHIV DER PHARMAZIE, 1997, 330 (06) : 190 - 198
  • [4] SYNTHESIS OF VINCA ALKALOIDS AND RELATED-COMPOUNDS .31. UNUSUAL POLONOVSKI REACTION OF SOME VINCA ALKALOIDS
    MOLDVAI, I
    VEDRES, A
    TOTH, G
    SZANTAY, C
    SZANTAY, C
    TETRAHEDRON LETTERS, 1986, 27 (24) : 2775 - 2778
  • [5] SYNTHESIS OF VINCA ALKALOIDS AND RELATED-COMPOUNDS .17. CHIRAL SYNTHESIS OF VINCA ALKALOIDS FROM L-TRYPTOPHAN
    SZABO, L
    SAPI, J
    NOGRADI, K
    KALAUS, G
    SZANTAY, C
    TETRAHEDRON, 1983, 39 (22) : 3749 - 3753
  • [6] SYNTHESIS OF VINCA ALKALOIDS AND RELATED-COMPOUNDS .72. SYNTHESIS OF (-)-VINCINONE
    SZABO, L
    KALAUS, G
    SZANTAY, C
    ACH-MODELS IN CHEMISTRY, 1994, 131 (3-4): : 541 - 542
  • [7] SYNTHESIS OF VINCA ALKALOIDS AND RELATED-COMPOUNDS .17. SYNTHESIS OF DEETHYLCATHARANTHINE
    SZANTAY, C
    KEVE, T
    BOLCSKEI, H
    ACS, T
    TETRAHEDRON LETTERS, 1983, 24 (49) : 5539 - 5540
  • [8] SYNTHESIS OF VINCA ALKALOIDS AND RELATED COMPOUNDS, .5. SYNTHESIS OF ETHYL (+/-)-APOVINCAMINATE
    KALAUS, G
    GYORY, P
    SZABO, L
    SZANTAY, C
    ACTA CHIMICA ACADEMIAE SCIENTARIUM HUNGARICAE, 1978, 97 (04): : 429 - 438
  • [9] Synthesis of vinca alkaloids and related compounds .80. Synthesis of (+)-Vincine and (+)-Apovincine
    Szabo, L
    Kalaus, G
    Szantay, C
    NATURAL PRODUCT LETTERS, 1996, 8 (04): : 237 - 240
  • [10] SYNTHESIS OF VINCA ALKALOIDS AND RELATED COMPOUNDS .3. STEREOSELECTIVE SYNTHESIS OF ISOVINCINE
    KALAUS, G
    SZABO, L
    HORVATH, J
    SZANTAY, C
    HETEROCYCLES, 1977, 6 (03) : 321 - 325