Synthesis of vinca alkaloids and related compounds -: part 94 [1].: Epimerization of compounds with aspidospermane and D-secoaspidospermane skeleton

被引：11
作者：
Kalaus, G
Juhász, I
Éles, J
Greiner, I
Kajtár-Peredy, M
Brlik, J
Szabó, L
Szántay, C
机构：
[1] Tech Univ Budapest, Dept Organ Chem, H-1521 Budapest, Hungary
[2] Gedeon Richter Ltd, Chem Works, H-1103 Budapest, Hungary
[3] Hungarian Acad Sci, Chem Res Ctr, Inst Chem, H-1525 Budapest, Hungary
来源：
JOURNAL OF HETEROCYCLIC CHEMISTRY | 2000年 / 37卷 / 02期
关键词：
D O I：
10.1002/jhet.5570370205
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The individual epimerization steps of vincadifformine (1), deethylvincadifformine isomers (2,3), their synthetic intermediates (4-13) as well as that of simpler compounds with D-secoaspidospermane skeleton (15-17) were studied a) in protic medium (boiling deuteroacetic acidic) and b) under reductive (with sodium borodeuteride in boiling acetic acid, or with sodium borohydride in boiling deuteroacetic acid) conditions.
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页码：245 / 251
页数：7
相关论文
共 19 条
  • [1] Cordell G.A., 1979, ALKALOIDS, V17, P199
  • [2] HONTY K, IN PRESS HETEROCYCLE
  • [3] INOUE I, 1970, Journal of the Chemical Society Section C Organic Chemistry, P602, DOI 10.1039/j39700000602
  • [4] SYNTHESIS OF VINCA ALKALOIDS AND RELATED-COMPOUNDS .63. A NEW SYNTHETIC PATHWAY FOR PREPARING ALKALOIDS AND RELATED-COMPOUNDS WITH THE ASPIDOSPERMA SKELETON - TOTAL SYNTHESES OF (+/-)-VINCADIFFORMINE, (+/--TABERSONINE, AND (+/-)-3-OXOTABERSONINE
    KALAUS, G
    GREINER, I
    KAJTARPEREDY, M
    BRLIK, J
    SZABO, L
    SZANTAY, C
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (06) : 1434 - 1442
  • [5] Kalaus G, 1998, HETEROCYCLES, V47, P205
  • [6] Synthesis of vinca alkaloids and related compounds.: 90.: New results in the synthesis of alkaloids with the aspidospermane skeleton.: First total synthesis of (±)-3-oxominovincine
    Kalaus, G
    Juhász, I
    Greiner, I
    Kajtár-Peredy, M
    Brlik, J
    Szabó, L
    Szántay, C
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (26) : 9188 - 9191
  • [7] SYNTHESIS OF VINCA ALKALOIDS AND RELATED-COMPOUNDS .64. TOTAL SYNTHESES OF (+/-)-PSEUDOVINCADIFFORMINE AND (+/-)-20-EPIPSEUDOVINCADIFFORMINE
    KALAUS, G
    GREINER, I
    KAJTARPEREDY, M
    BRLIK, J
    SZABO, L
    SZANTAY, C
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (22) : 6076 - 6082
  • [8] KALAUS G, 1995, LIEBIGS ANN, P1245
  • [9] SYNTHESIS OF VINCA ALKALOIDS AND RELATED-COMPOUNDS .76. SYNTHESIS AND RING TRANSFORMATIONS OF COMPOUNDS WITH THE ASPIDOSPERMANE AND D-NORASPIDOSPERMANE SKELETON - A FORMAL SYNTHESIS OF (+/-)-12-DEMETHOXY-N(1)-ACETYL-CYLINDROCARINE
    KALAUS, G
    VAGO, I
    GREINER, I
    PEREDY, MK
    BRLIK, J
    SZABO, L
    SZANTAY, C
    [J]. NATURAL PRODUCT LETTERS, 1995, 7 (03): : 197 - 204
  • [10] TOTAL SYNTHESIS OF (+/-)-6,7-DIDEHYDROASPIDOSPERMINE
    KLIOZE, SS
    DARMORY, FP
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (11) : 1588 - 1592
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