Total synthesis of suaveoline and norsuaveoline via intramolecular oxazole-olefin Diels-Alder reaction

被引：36
|
作者：
Ohba, M [1 ]
Natsutani, I
Sakuma, T
机构：
[1] Kanazawa Univ, Adv Sci Res Ctr, Kanazawa, Ishikawa 9201192, Japan
[2] Kanazawa Univ, Fac Pharmaceut Sci, Kanazawa, Ishikawa 9201192, Japan
来源：
TETRAHEDRON LETTERS | 2004年 / 45卷 / 34期
关键词：
alkaloids; amino acids and derivatives; Diels-Alder reactions; indoles; oxazoles;
D O I：
10.1016/j.tetlet.2004.06.108
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Total synthesis of two Rauwolfia alkaloids, suaveoline (1) and norsuaveoline (2), has been achieved through a highly stereoselective route starting from L-tryptophan methyl ester (9) and exploiting the intramolecular Diels-Alder reaction of the oxazole-olefin 16. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6471 / 6474
页数：4
相关论文
共 50 条
  • [31] Total Synthesis of the Neoclerodane Diterpene Salvinorin A via an Intramolecular Diels-Alder Strategy
    Wang, Yuzhou
    Metz, Peter
    ORGANIC LETTERS, 2018, 20 (11) : 3418 - 3421
  • [32] Synthesis of antitumor lycorines by intramolecular Diels-Alder reaction
    Perez, D
    Bures, G
    Guitian, E
    Castedo, L
    JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (05): : 1650 - 1654
  • [33] Total synthesis of the proposed structure of lepadiformine via intramolecular N-acylnitroso Diels-Alder reaction
    Abe, H
    Aoyagi, S
    Kibayashi, C
    TETRAHEDRON LETTERS, 2000, 41 (08) : 1205 - 1208
  • [34] ALKALOID SYNTHESIS VIA INTRAMOLECULAR IMINO DIELS-ALDER CHEMISTRY - TOTAL SYNTHESIS OF (+/-)-EBURNAMONINE
    KAUFMAN, MD
    GRIECO, PA
    JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (24): : 7197 - 7198
  • [35] A concise formal total synthesis of mappicine and nothapodytine B via an intramolecular hetero Diels-Alder reaction
    Toyota, M
    Komori, C
    Ihara, M
    JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (21): : 7110 - 7113
  • [36] SYNTHESIS OF TETRAHYDROFUROCARBAZOLONES VIA INTRAMOLECULAR DIELS-ALDER REACTIONS
    MADALENGOITIA, JS
    MACDONALD, TL
    TETRAHEDRON LETTERS, 1993, 34 (39) : 6237 - 6240
  • [37] SYNTHESIS OF HYDROISOINDOLES VIA INTRAMOLECULAR DIELS-ALDER REACTIONS
    GUY, A
    GRAILLOT, Y
    TETRAHEDRON LETTERS, 1990, 31 (50) : 7315 - 7318
  • [38] Total synthesis of 14β-fluorosteroids via a transannular Diels-Alder reaction
    Beaubien, S
    Deslongchamps, P
    CANADIAN JOURNAL OF CHEMISTRY, 2006, 84 (01) : 29 - 48
  • [39] Concise enantioselective synthesis of wine lactone via intramolecular Diels-Alder reaction
    Ohkubo, Yasutaka
    Masuda, Yui
    Ogura, Yusuke
    Takikawa, Hirosato
    Watanabe, Hidenori
    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2021, 85 (06) : 1390 - 1394
  • [40] Concise enantioselective synthesis of wine lactone via intramolecular Diels-Alder reaction
    Ohkubo, Yasutaka
    Masuda, Yui
    Ogura, Yusuke
    Takikawa, Hirosato
    Watanabe, Hidenori
    Bioscience, Biotechnology and Biochemistry, 2021, 85 (06): : 1390 - 1394
12345