Enantioselective Synthesis of Jaspine B (Pachastrissamine) and Its C-2 and/or C-3 Epimers

被引:44
|
作者
Llaveria, Josep [1 ]
Diaz, Yolanda [1 ]
Isabel Matheu, M. [1 ]
Castillon, Sergio [1 ]
机构
[1] Univ Rovira & Virgili, Dept Quim Analit & Quim Organ, Fac Quim, Tarragona 43007, Spain
关键词
Natural products; Enantioselectivity; Metathesis; Dihydroxylation; PALLADIUM-CATALYZED DYKAT; D-LYXO-PHYTOSPHINGOSINE; STEREOSELECTIVE-SYNTHESIS; CYTOTOXIC ANHYDROPHYTOSPHINGOSINE; ASYMMETRIC-SYNTHESIS; MARINE SPONGE; 2-EPI-JASPINE-B; SPHINGOSINE; EFFICIENT;
D O I
10.1002/ejoc.201001477
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Jaspine B and its C-2 and/or C3 epimers have been enantio-selectively prepared from butadiene monoepoxide through a synthetic procedure consisting of allylic amination by palla-dium-catalyzed dynamic kinetic asymmetric transformation, cross metathesis, and stereoselective dihydroxylation as key steps.
引用
收藏
页码:1514 / 1519
页数:6
相关论文
共 50 条
  • [1] Stereoselective Synthesis and Biological Studies of the C2 and C3 Epimer and the Enantiomer of Pachastrissamine (Jaspine B)
    Jayachitra, G.
    Sudhakar, N.
    Anchoori, Ravi Kumar
    Rao, B. Venkateswara
    Roy, Sayantani
    Banerjee, Rajkumar
    SYNTHESIS-STUTTGART, 2010, (01): : 115 - 119
  • [2] Synthesis of pachastrissamine (jaspine B) and its derivatives by the late-stage introduction of the C-2 alkyl side-chains using olefin cross metathesis
    Yoshimitsu, Yuji
    Miyagaki, Jun
    Oishi, Shinya
    Fujii, Nobutaka
    Ohno, Hiroaki
    TETRAHEDRON, 2013, 69 (21) : 4211 - 4220
  • [3] Asymmetric synthesis of Pachastrissamine (Jaspine B) and its diastereomers via η3-allylpalladium intermediates
    Passiniemi, Mikko
    Koskinen, Ari M. P.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (06) : 1774 - 1783
  • [4] Practical Synthesis of Pachastrissamine (Jaspine B), 2-epi-Pachastrissamine, and the 2-epi-Pyrrolidine Analogue
    Fujiwara, Tomoya
    Liu, Bo
    Niu, Wenqi
    Hashimoto, Kazuki
    Nambu, Hisanori
    Yakura, Takayuki
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2016, 64 (02) : 179 - 188
  • [5] Stereoselective synthesis of Jaspine B and its C2 epimer from Garner aldehyde
    Jana, Amit Kumar
    Panda, Gautam
    RSC ADVANCES, 2013, 3 (37) : 16795 - 16801
  • [6] Synthesis of Decytospolide A, B and Their C-3 Epimers Using Stereoselective Oxypalladation
    Kurogome, Yuji
    Hattori, Yasunao
    Makabe, Hidefumi
    SYNTHESIS-STUTTGART, 2016, 48 (05): : 765 - 771
  • [7] Stereodivergent synthesis of jaspine B and its isomers using a carbohydrate-derived alkoxyallene as C3-building block
    Schmiedel, Volker M.
    Stefani, Stefano
    Reissig, Hans-Ulrich
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2013, 9 : 2564 - 2569
  • [8] Stereoselective total synthesis of Jaspine B (Pachastrissamine) utilizing iodocyclization and an investigation of its cytotoxic activity
    Ghosal, Partha
    Ajay, Sama
    Meena, Sanjeev
    Sinha, Sudhir
    Shaw, Arun K.
    TETRAHEDRON-ASYMMETRY, 2013, 24 (15-16) : 903 - 908
  • [9] Nitrolaldol reaction of (R)-2,3-cyclohexylideneglyceraldehyde: a simple and stereoselective synthesis of the cytotoxic Pachastrissamine (Jaspine B)
    Vichare, Prasad
    Chattopadhyay, Angshuman
    TETRAHEDRON-ASYMMETRY, 2010, 21 (16) : 1983 - 1987
  • [10] A common approach to the total synthesis of L-arabino-, L-ribo-C18-phytosphingosines, ent-2-epi-jaspine B and 3-epi-jaspine B from D-mannose
    Martinkova, Miroslava
    Pomikalova, Kvetoslava
    Gonda, Jozef
    Vilkova, Maria
    TETRAHEDRON, 2013, 69 (38) : 8228 - 8244