Synthesis of enantiomerically pure (-)-(S)-brevicolline

被引:18
作者
Mahboobi, S [1 ]
Wiegrebe, W [1 ]
Popp, A [1 ]
机构
[1] Univ Regensburg, Inst Pharm, D-93040 Regensburg, Germany
来源
JOURNAL OF NATURAL PRODUCTS | 1999年 / 62卷 / 04期
关键词
D O I
10.1021/np980492h
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
(-)-(S)-Brevicolline (1) and related beta-carbolines were synthesized using an enantiomerically pure Michael-acceptor synthon (3). Subsequent Pictet-Spengler reaction afforded the tetrahydro-beta-carboline skeleton, which, in turn, was transformed to the beta-carboline by catalytic dehydrogenation.
引用
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页码:577 / 579
页数:3
相关论文
共 26 条
  • [1] ALVAREZ M, 1991, HETEROCYCLES, V32, P1391
  • [2] Baker B. J., 1996, Alkaloids: Chemical and Biological Perspectives, V10, P357
  • [3] BATCH A, 1988, J ORG CHEM, V36, P872
  • [4] BAUMGARTH M, 1973, CHEM ZTG, V97, P217
  • [5] Behforouz M., 1997, U. S. Patent, Patent No. [U.S 5646150 A, 5646150, 5,646,150]
  • [6] URINARY AND BRAIN BETA-CARBOLINE-3-CARBOXYLATES AS POTENT INHIBITORS OF BRAIN BENZODIAZEPINE RECEPTORS
    BRAESTRUP, C
    NIELSEN, M
    OLSEN, CE
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA-BIOLOGICAL SCIENCES, 1980, 77 (04): : 2288 - 2292
  • [7] CHLECKER W, 1995, SYNTHESIS-STUTTGART, P1225
  • [8] DAUGAN ACM, 1996, Patent No. 32003
  • [9] LAZURJEVSKI G, 1976, HETEROCYCLES, V4, P1783, DOI 10.3987/R-1976-11-1783
  • [10] LETTE E, 1979, J CHEM SOC CHEM COMM, P821