Enantioselective total synthesis of 3-epi-ottelione A

被引：11
|
作者：
Araki, H
Inoue, M
Katoh, T [1 ]
机构：
[1] Tokyo Inst Technol, Dept Elect Chem, Yokohama, Kanagawa 2268502, Japan
[2] Sagami Chem Res Ctr, Kanagawa 2521193, Japan
来源：
SYNLETT | 2003年 / 15期
关键词：
3-epi-ottelione A; total synthesis; otteliones A and B; natural products; antitumor agents;
D O I：
10.1055/s-2003-42114
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An enantioselective total synthesis of (+)-3-epi-ottelione A (2), the earlier proposed stereostructure of the antitumor natural product ottelione A (4), was achieved for the first time starting from the known tetracyclic compound 9. The synthesis involves the following three crucial steps: (i) a coupling reaction of aldehyde 8 and aryllithium 7 to introduce the aromatic portion, (ii) base-induced lactol-opening/epimerization at the C1 position of 6 to deliver the requisite hydrindane 15, and (iii) Corey-Winter's reductive olefination of the cyclic thiocarbonate 19 to install the C5-C6 double bond.
引用
收藏
页码：2401 / 2403
页数：3
相关论文
共 50 条
  • [1] Enantioselective total synthesis of (+)-ottelione A, (-)-ottelione B, (+)-3-epi-ottelione a and preliminary evaluation of their antitumor activity
    Araki, Hiroshi
    Inoue, Munenori
    Suzuki, Takeyuki
    Yamori, Takao
    Kohno, Michiaki
    Watanabe, Kazuhiro
    Abe, Hideki
    Katoh, Tadashi
    CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (35) : 9866 - 9881
  • [2] Enantioselective total synthesis of 1-epi-pathylactone A
    Chanu, Angeline
    Safir, Imad
    Basak, Ramkrishna
    Chiaroni, Angele
    Arseniyadis, Simeon
    ORGANIC LETTERS, 2007, 9 (07) : 1351 - 1354
  • [3] Enantioselective total synthesis of (+)-brefeldin A and 7-epi-brefeldin A
    Wu, YK
    Shen, X
    Yang, YQ
    Hu, Q
    Huang, JH
    JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (11): : 3857 - 3865
  • [4] Enantioselective total syntheses of (+)- and (-)-ottelione A and (+)- and (-)-ottelione B. Absolute configuration of the novel, biologically active natural products
    Mehta, G
    Islam, K
    TETRAHEDRON LETTERS, 2003, 44 (35) : 6733 - 6736
  • [5] Enantioselective Formal Synthesis of (+)-Cycloclavine and Total Synthesis of (+)-5-epi-Cycloclavine
    Wang, Wei
    Mi, Yang
    Cao, Xiao-Ping
    Shi, Zi-Fa
    ORGANIC LETTERS, 2019, 21 (17) : 6603 - 6607
  • [6] Enantioselective total synthesis of (+)-duocarmycin A, epi-(+)-duocarmycin A, and their unnatural enantiomers
    Boger, DL
    McKie, JA
    Nishi, T
    Ogiku, T
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (09) : 2301 - 2302
  • [7] Short Enantioselective Total Synthesis of TatananA and 3-epi-TatananA Using Assembly-Line Synthesis
    Noble, Adam
    Roesner, Stefan
    Aggarwal, Varinder K.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (51) : 15920 - 15924
  • [8] Enantioselective total synthesis of parnafungin A1 and 10a-epi-hirtusneanine
    Sun, Jiawei
    Gu, Wei
    Yang, He
    Tang, Wenjun
    CHEMICAL SCIENCE, 2021, 12 (30) : 10313 - 10320
  • [9] Enantioselective total synthesis of (-)-neovibsanin G and (-)-14-epi-neovibsanin G
    Mak, Jeffrey Y. W.
    Williams, Craig M.
    CHEMICAL COMMUNICATIONS, 2012, 48 (02) : 287 - 289
  • [10] Towards the synthesis of prevezol C: total enantioselective synthesis of (-)-2-epi-prevezol C
    Blair, Michael
    Forsyth, Craig M.
    Tuck, Kellie L.
    TETRAHEDRON LETTERS, 2010, 51 (37) : 4808 - 4811
12345