Enantio selective total synthesis of the novel antiproliferative metabolite (+)-hexacyclinol

被引:25
|
作者
Mehta, Goverdhan [1 ]
Roy, Subhrangsu [1 ]
机构
[1] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India
关键词
D O I
10.1016/j.tetlet.2008.01.014
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An enantioselective total synthesis of the novel bioactive epoxyquinone natural product (+)-hexacyclinol, exhibiting promising growth inhibiting activity against cancer cell lines, has been accomplished from a readily available chiron derived from the Diels-Alder adduct of cyclopentadiene and p-benzoquinone. (c) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1458 / 1460
页数:3
相关论文
共 50 条
  • [1] Hexacyclinol, a new antiproliferative metabolite of Panus rudis HKI 0254
    Schlegel, B
    Härtl, A
    Dahse, HM
    Gollmick, FA
    Gräfe, U
    Dorfelt, H
    Kappes, B
    JOURNAL OF ANTIBIOTICS, 2002, 55 (09): : 814 - 817
  • [2] Total synthesis and structure assignment of (+)-hexacyclinol
    Porco, John A., Jr.
    Su, Shun
    Lei, Xiaoguang
    Bardhan, Sujata
    Rychnovsky, Scott D.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (35) : 5790 - 5792
  • [3] Total synthesis of a novel cytotoxic metabolite gymnastatin A
    Gurjar, MK
    Bhaket, P
    HETEROCYCLES, 2000, 53 (01) : 143 - 149
  • [4] On the traces of absolute enantio selective synthesis
    Barabas, Bela
    Caglioti, Luciano
    Faglioni, Francesco
    Florini, Nicola
    Lazzeretti, Paolo
    Maioli, Marco
    Micskei, Karoly
    Rabai, Gyula
    Taddei, Ferdinando
    Zucchi, Claudia
    Palyi, Gyula
    COMPUTATION IN MODERN SCIENCE AND ENGINEERING VOL 2, PTS A AND B, 2007, 2 : 1150 - +
  • [5] Total synthesis of (-)-microcarpalide, a novel microfilament disrupting metabolite
    Davoli, P
    Spaggiari, A
    Castagnetti, L
    Prati, F
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (01) : 38 - 47
  • [6] Enantio- and Diastereocontrolled Total Synthesis of (+)-Strictifolione
    Kumar, Pradeep
    Pandey, Menaka
    Gupta, Priti
    Naidu, S. Vasudeva
    Dhavale, Dilip D.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (36) : 6993 - 7004
  • [7] Enantio- and diastereocontrolled total synthesis of (+)-boronolide
    Kumar, P
    Naidu, SV
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (10): : 3935 - 3941
  • [8] Total synthesis of (+)-curacin A, a novel antimitotic metabolite from a cyanobacterium
    Muir, JC
    Pattenden, G
    Ye, T
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (20): : 2243 - 2250
  • [9] Structure and total synthesis of aspernigerin: A novel cytotoxic endophyte metabolite
    Shen, Li
    Ye, Yong-Hao
    Wang, Xiao-Ting
    Zhu, Hai-Liang
    Xu, Chen
    Song, Yong-Cun
    Li, Hai
    Tan, Ren-Xiang
    CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (16) : 4393 - 4396
  • [10] ENANTIO-SELECTIVE AND DIASTEREO-SELECTIVE SYNTHESIS OF SPIROCYCLIC COMPOUNDS
    SUEMUNE, H
    MAEDA, K
    KATO, K
    SAKAI, K
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (23): : 3441 - 3447