Biomimetic approach to perophoramidine and communesin via an intramolecular cyclopropanation reaction

被引：99
作者：
Yang, J
Song, H
Xiao, X
Wang, J
Qin, Y [1 ]
机构：
[1] W China Sch Pharm, Dept Chem Med Nat Prod, Chengdu 610041, Peoples R China
[2] W China Sch Pharm, Key Lab Drug Targeting, Chengdu 610041, Peoples R China
[3] Sichuan Univ, Natl Key Lab Biotherapy, Chengdu 610041, Peoples R China
来源：
ORGANIC LETTERS | 2006年 / 8卷 / 10期
关键词：
D O I：
10.1021/ol0607138
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Starting from tryptamine 4 and isatin 5, a biomimetic approach to the pentacyclic substructure 1 of perophoramidine and communesin was developed. The key steps were to create a stable three/six bicyclic system 2 on the 2,3-double bond of an indole derivative 3 by an intramolecular cyclopropanation, followed by ring opening of the resulting cyclopropane ring with the in situ generated amine group of an aniline.
引用
收藏
页码：2187 / 2190
页数：4
相关论文
共 23 条
  • [1] An approach to the total synthesis of the marine ascidian metabolite perophoramidine via a halogen-selective tandem Heck/carbonylation strategy
    Artman, GD
    Weinreb, SM
    [J]. ORGANIC LETTERS, 2003, 5 (09) : 1523 - 1526
  • [2] SYNTHESIS OF N-CARBOMETHOXYMETHANOCARBAZOLE
    ASHMORE, JW
    RADLICK, PC
    HELMKAMP, GK
    [J]. SYNTHETIC COMMUNICATIONS, 1976, 6 (06) : 399 - 402
  • [3] A synthetic approach to nomofungin/communesin B
    Crawley, SL
    Funk, RL
    [J]. ORGANIC LETTERS, 2003, 5 (18) : 3169 - 3171
  • [4] D'Amours D, 2001, J CELL SCI, V114, P3771
  • [5] Communesins G and H, new alkaloids from the psychrotolerant fungus Penicillium rivulum
    Dalsgaard, PW
    Blunt, JW
    Munro, MHG
    Frisvad, JC
    Christophersen, C
    [J]. JOURNAL OF NATURAL PRODUCTS, 2005, 68 (02): : 258 - 261
  • [6] ELECTROPHILIC CYCLOPROPANES IN ORGANIC-SYNTHESIS
    DANISHEFSKY, S
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1979, 12 (02) : 66 - 72
  • [7] RING-EXPANSION OF A DIHALOGENOCARBENE ADDUCT OF A CYCLOHEPTENE DERIVATIVE AND THE CORRESPONDING RETRO-REACTION
    DHANAK, D
    KURODA, R
    REESE, CB
    [J]. TETRAHEDRON LETTERS, 1987, 28 (16) : 1827 - 1830
  • [8] Doyle M. P., 1998, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides
  • [9] Total synthesis of (±)-perophoramidine
    Fuchs, JR
    Funk, RL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (16) : 5068 - 5069
  • [10] Stereoselective synthesis of novel conformationally restricted β- and γ-amino acids
    Gnad, F
    Poleschak, M
    Reiser, O
    [J]. TETRAHEDRON LETTERS, 2004, 45 (22) : 4277 - 4280
123