Synthesis and Assignment of the Absolute Configuration of Indenotryptoline Bisindole Alkaloid BE-54017

被引：32
|
作者：
Kimura, Tomoyuki [1 ]
Kanagaki, Shuhei [2 ]
Matsui, Yusuke [2 ]
Imoto, Masaya [2 ]
Watanabe, Takumi [1 ]
Shibasaki, Masakatsu [1 ]
机构：
[1] Inst Microbial Chem, Shinagawa Ku, Tokyo 1410021, Japan
[2] Keio Univ, Dept Biosci & Informat, Fac Sci & Technol, Yokohama, Kanagawa 2238522, Japan
来源：
ORGANIC LETTERS | 2012年 / 14卷 / 17期
关键词：
ISOGRANULATIMIDE ANALOGS; BIOLOGICAL-ACTIVITY; INHIBITORS; DIHYDROXYLATION; STAUROSPORINE; BIOSYNTHESIS; REBECCAMYCIN; PRODUCTS; OLEFINS;
D O I：
10.1021/ol3019314
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Synthesis of the indenotryptoline bisindole alkaloid, BE-54017, was accomplished using osmium-promoted cis-dihydroxylation of maleimide as a key step. After optical resolution, the absolute configuration of this molecule was determined by comparing its optical otation and HPLC profile to those obtained for BE-54017 derived from enantiopure cladoniamide A, whose stereochemistry has been reported previously. BE-54017 with the correct absolute stereochemistry induced apoptosis of epidermal growth factor (EGF)-stimulated EGF receptor overexpressing A431 cells and inhibited vacuolar-type H+-ATPase (V-ATPase).
引用
收藏
页码：4418 / 4421
页数：4
相关论文
共 50 条
  • [1] Total synthesis of the coccinellid alkaloid (-)-adalinine and the assignment of its absolute configuration
    Yamazaki, N
    Ito, T
    Kibayashi, C
    TETRAHEDRON LETTERS, 1999, 40 (04) : 739 - 742
  • [2] Absolute configuration assignment to anticancer Amaryllidaceae alkaloid jonquailine
    Vergura, Stefania
    Santoro, Ernesto
    Masi, Marco
    Evidente, Antonio
    Scafato, Patrizia
    Superchi, Stefano
    Mazzeo, Giuseppe
    Longhi, Giovanna
    Abbate, Sergio
    FITOTERAPIA, 2018, 129 : 78 - 84
  • [3] First total synthesis and assignment of the absolute configuration of the neuronal cell protecting alkaloid carbazomadurin B
    Knöll, J
    Knölker, HJ
    SYNLETT, 2006, (04) : 651 - 653
  • [4] Assignment of the Absolute Configuration and Total Synthesis of (+)-Caripyrin
    Andernach, Lars
    Opatz, Till
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (22) : 4780 - 4784
  • [5] Total Synthesis of Bipenicilisorin and Assignment of the Absolute Configuration
    Fukuda, Eigo
    Fujiwara, Ibuki
    Maruno, Shoki
    Motomura, Kaiki
    Endo, Seiya
    Iwasaki, Arihiro
    Fukuta, Tatsuya
    Nakayama, Atsushi
    Shinada, Tetsuro
    JOURNAL OF NATURAL PRODUCTS, 2024, 87 (05): : 1394 - 1400
  • [6] (-)-ALANGIMARCKINE - SYNTHESIS AND ABSOLUTE-CONFIGURATION OF AN ALANGIUM ALKALOID
    FUJII, T
    KOGEN, H
    OHBA, M
    TETRAHEDRON LETTERS, 1978, (34) : 3111 - 3114
  • [7] SYNTHESIS AND ABSOLUTE-CONFIGURATION OF THE ARISTOTELIA ALKALOID PEDUNCULARINE
    KLAVER, WJ
    HIEMSTRA, H
    SPECKAMP, WN
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (07) : 2588 - 2595
  • [8] Total synthesis and absolute stereochemical assignment of (+)- and (-)-galbulimima alkaloid 13
    Movassaghi, Mohammad
    Hunt, Diana K.
    Tjandra, Meiliana
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (25) : 8126 - 8127
  • [9] Synthesis of (-)-nakamurol A and assignment of absolute configuration of diterpenoid (+)-nakamurol A
    Díaz, S
    Cuesta, J
    González, A
    Bonjoch, J
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (19): : 7400 - 7406
  • [10] Enantioselective Total Synthesis and Absolute Configuration Assignment of (+)-Toxicodenane A
    Qin, Xu-Long
    Wu, Guo-Jie
    Han, Fu-She
    ORGANIC LETTERS, 2021, 23 (21) : 8570 - 8574
12345