Synthesis of chiral 3-substituted hexahydropyrroloindoline via intermolecular cyclopropanation

被引:54
|
作者
Hao Song
Jun Yang
Wei Chen
Yong Qin [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, State Key Lab Biotherapy, Chengdu 610041, Peoples R China
关键词
D O I
10.1021/ol062489s
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new and efficient synthetic route to chiral 3- substituted hexahydropyrroloindoline 18 possessing absolute configurations in accordance with indole alkaloids has been developed from readily available L- tryptophan. The key step relies on the one- pot cascade reaction of oxazolidinone 17 with diazoester, which proceeds through intermolecular cyclopropanation, ring opening, and cyclization.
引用
收藏
页码:6011 / 6014
页数:4
相关论文
共 50 条
  • [1] Synthesis of chiral 3-substituted isoxazolidines.
    Farr, RN
    TETRAHEDRON LETTERS, 1998, 39 (3-4) : 195 - 196
  • [2] Synthesis of substituted tetrahydrofurans via intermolecular reactions of γ-chlorocarbanions of 3-substituted 3-chloro-propylphenyl sulfones with aldehydes
    Brandt, Agnieszka
    Wojtasiewicz, Anna
    Sniezek, Marcin
    Makosza, Mieczyslaw
    TETRAHEDRON, 2010, 66 (18) : 3378 - 3385
  • [3] SYNTHESIS AND POLYMERIZATION OF THIOPHENES 3-SUBSTITUTED BY CHIRAL CHAINS
    SCHULZ, E
    BETHMONT, V
    FAHMI, K
    FACHE, F
    LEMAIRE, M
    JOURNAL DE CHIMIE PHYSIQUE ET DE PHYSICO-CHIMIE BIOLOGIQUE, 1995, 92 (04) : 783 - 786
  • [4] Chiral Bronsted acid catalyzed enantioselective intermolecular desymmetrizations of 3-substituted azetidines
    Wang, Zhaobin
    Sun, Jianwei
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [5] Synthesis of chiral 3-substituted indanones via an enantioselective reductive-heck reaction
    Minatti, Ana
    Zheng, Xiaolai
    Buchwald, Stephen L.
    JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (24): : 9253 - 9258
  • [6] Highly Enantioselective Synthesis of Chiral Cyclopropyl Nucleosides via Catalytic Asymmetric Intermolecular Cyclopropanation
    Li, Jian-Ping
    Zhao, Guo-Feng
    Wang, Hai-Xia
    Xie, Ming-Sheng
    Qu, Gui-Rong
    Guo, Hai-Ming
    ORGANIC LETTERS, 2017, 19 (24) : 6494 - 6497
  • [7] Chiral bifunctional organocatalysts for enantioselective synthesis of 3-substituted isoindolinones
    Hu, Xiao-Mu
    Zhang, Rui
    Dong, Hai
    Jia, Yan-Yan
    Bao, Guo-Qiang
    Wang, Ping-An
    RSC ADVANCES, 2023, 13 (35) : 24460 - 24465
  • [8] Synthesis of chiral 3-substituted phthalides via rhodium(I)-catalyzed crossed alkyne cyclotrimerisation
    Witulski, B
    Zimmermann, A
    SYNLETT, 2002, (11) : 1855 - 1859
  • [9] Asymmetric synthesis of 3-substituted pyrrolidones via α-alkylation of a chiral non-racemic γ-lactam
    Baussanne, I
    Travers, C
    Royer, J
    TETRAHEDRON-ASYMMETRY, 1998, 9 (05) : 797 - 804
  • [10] Synthesis of useful chiral building blocks via efficient enantioselective desymmetrization of 3-substituted oxetanes
    Wang, Zhaobin
    Chen, Zhilong
    Sun, Jianwei
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245