A Novel Asymmetric Synthesis of (+)-Deoxytylophorinine

被引:2
|
作者
Lv, Haining [1 ,2 ]
Xu, Song [1 ,2 ]
Ma, Shuanggang [1 ,2 ]
Liu, Yunbao [1 ,2 ]
Li, Yong [1 ,2 ]
Qu, Jing [1 ,2 ]
Yu, Shishan [1 ,2 ]
机构
[1] Chinese Acad Med Sci, Inst Mat Med, State Key Lab Bioact Subst & Funct Nat Med, Beijing 100050, Peoples R China
[2] Peking Union Med Coll, Beijing 100050, Peoples R China
来源
SYNTHESIS-STUTTGART | 2015年 / 47卷 / 10期
关键词
phenanthroindolizidine alkaloids; (+)-deoxytylophorinine; asymmetric synthesis; anticancer agents; non-proteinogenic -amino acids; PHENANTHROINDOLIZIDINE ALKALOIDS; AMINO-ACIDS; PHENANTHROQUINOLIZIDINES; CRYPTOPLEURINE; COMPLEXES; NI(II);
D O I
10.1055/s-0034-1380137
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel asymmetric synthesis of a phenanthroindolizidine alkaloid, (+)-deoxytylophorinine, is reported, which uses a chiral nickel(II) complex of a glycine Schiff base to synthesize a substituted (R)-3-phenanthrylalanine as a key intermediate and Meldrum's acid to construct the E ring.
引用
收藏
页码:1399 / 1404
页数:6
相关论文
共 50 条
  • [31] Design, synthesis, and application of novel chiral ONN ligands for asymmetric alkylation
    Katharina Bica
    Sonja Leder
    Kurt Mereiter
    Peter Gaertner
    Monatshefte für Chemie - Chemical Monthly, 2013, 144 : 447 - 453
  • [32] Asymmetric synthesis
    Agbossou-Niedercorn, F
    ACTUALITE CHIMIQUE, 2002, (5-6): : 80 - 85
  • [33] A Novel Method for the Synthesis of Newfangled Asymmetric Schiff Bases from -amino Acids under Ultrasonic Conditions and in Aqueous Medium
    Sendil, Kivilcim
    Tekin, Turgay
    Goksu, Haydar
    Oguz, Mehmet
    Anil, Baris
    Gultekin, Mehmet Serdar
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2016, 63 (09) : 808 - 817
  • [34] Asymmetric synthesis of α,β-substituted β-aminoalkanamides and stereochemical determination
    Capriati, Vito
    Degennaro, Leonardo
    Florio, Saverio
    Luisi, Renzo
    Cuocci, Corrado
    TETRAHEDRON LETTERS, 2007, 48 (49) : 8655 - 8658
  • [35] Absolute Asymmetric Synthesis: Protected Substrate Oxidation
    Olsson, Susanne
    Bjoremark, Per Martin
    Kokoli, Theonitsa
    Sundberg, Jonas
    Lennartson, Anders
    McKenzie, Christine J.
    Hakansson, Mikael
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (13) : 5211 - 5219
  • [36] Catalytic Asymmetric Synthesis of γ-Substituted Vinyl Sulfones
    Lopez, Rosa
    Zalacain, Maitane
    Palomo, Claudio
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (08) : 2450 - 2457
  • [37] Asymmetric Synthesis of Cyclic Fluorinated Amino Acids
    Hao, Jing
    Milcent, Thierry
    Retailleau, Pascal
    Soloshonok, Vadim A.
    Ongeri, Sandrine
    Crousse, Benoit
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (27-28) : 3688 - 3692
  • [38] Progress in the Asymmetric Synthesis of Statine and Its Analogs
    Zhang, Wei
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2012, 32 (12) : 2203 - 2213
  • [39] A novel and highly efficient asymmetric synthesis of epoxides via chiral telluronium ylides
    Ou, WH
    Huang, ZZ
    SYNTHESIS-STUTTGART, 2005, (17): : 2857 - 2860
  • [40] A novel chiral base mediated glutarimide desymmetrisation: Application to the asymmetric synthesis of (-)-paroxetine
    Greenhalgh, DA
    Simpkins, NS
    SYNLETT, 2002, (12) : 2074 - 2076