A Versatile Total Synthesis of Trachycladines A and B and Their Analogues

被引：5
作者：
Peitsinis, Zisis V. [1 ]
Melidou, Dafni A. [1 ]
Stefanakis, John G. [1 ]
Evgenidou, Helen [1 ]
Koumbis, Alexandros E. [1 ]
机构：
[1] Aristotle Univ Thessaloniki, Dept Chem, Organ Chem Lab, Thessaloniki 54124, Greece
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 2014卷 / 36期
关键词：
Total synthesis; Natural products; Carbohydrates; Nucleosides; Glycosylation; NUCLEOSIDE NATURAL-PRODUCTS; EFFICIENT SYNTHESIS; PROGRESS; PURINE; SPONGE;
D O I：
10.1002/ejoc.201403091
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The synthesis of marine nucleosides trachycladines A and B and two nucleoside analogues was accomplished following a versatile and high-yielding scheme starting from D-ribose. The key step involved a regio- and stereoselective direct Vorbruggen glycosylation reaction between the appropriate nucleobase and a common intermediate, 2-C-methyl-D-5-deoxyribofuranose triacetate.
引用
收藏
页码：8160 / 8166
页数：7
相关论文
共 44 条
  • [1] Advances in the enantioselective synthesis of carbocyclic nucleosides
    Boutureira, Omar
    Isabel Matheu, M.
    Diaz, Yolanda
    Castillon, Sergio
    [J]. CHEMICAL SOCIETY REVIEWS, 2013, 42 (12) : 5056 - 5072
  • [2] Marine cyanobacteria - a prolific source of natural products
    Burja, AM
    Banaigs, B
    Abou-Mansour, E
    Burgess, JG
    Wright, PC
    [J]. TETRAHEDRON, 2001, 57 (46) : 9347 - 9377
  • [3] Efficient synthesis of an adenosine A2a agonist:: Glycosylation of 2-haloadenines and an N2-alkyl-6-chloroguanine
    Caddell, JM
    Chapman, AM
    Cooley, BE
    Downey, BP
    LeBlanc, MP
    Jackson, MM
    O'Connell, T
    Phung, HM
    Roper, TD
    Xie, SP
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (09) : 3212 - 3215
  • [4] Casu F, 2007, CURR ORG CHEM, V11, P999
  • [5] Concise total synthesis of two marine natural nucleosides: trachycladines A and B
    Ding, Haixin
    Li, Wei
    Ruan, Zhizhong
    Yang, Ruchun
    Mao, Zhijie
    Xiao, Qiang
    Wu, Jun
    [J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2014, 10 : 1681 - 1685
  • [6] Ebada SS, 2011, MINI-REV MED CHEM, V11, P225
  • [7] Asymmetric synthesis of 4′-epi-trachycladines A and B
    Enders, D
    Breuer, I
    Drosdow, E
    [J]. SYNTHESIS-STUTTGART, 2005, (19): : 3239 - 3244
  • [8] Ergoan I., 2000, J FAC PHARM ANKARA, V29, P1
  • [9] An improved approach to chiral cyclopentenone building blocks. Total synthesis of pentenomycin I and neplanocin A
    Gallos, JK
    Stathakis, CI
    Kotoulas, SS
    Koumbis, AE
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (17) : 6884 - 6890
  • [10] KUMUSINE, A CHLOROADENINE RIBOSIDE FROM A SPONGE, THEONELLA SP
    ICHIBA, T
    NAKAO, Y
    SCHEUER, PJ
    SATA, NU
    KELLYBORGES, M
    [J]. TETRAHEDRON LETTERS, 1995, 36 (23) : 3977 - 3980
12345