Stereoselective total synthesis of pachastrissamine (jaspine B)

被引:45
|
作者
Passiniemi, Mikko [1 ]
Koskinen, Ari M. P. [1 ]
机构
[1] Aalto Univ, Organ Chem Lab, FIN-02015 Espoo, Finland
关键词
natural products; enantio selective synthesis; pachastrissamine; cross metathesis; cyclization;
D O I
10.1016/j.tetlet.2007.12.014
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A short total synthesis of the cytotoxic natural product pachastrissamine is described. The synthesis includes eight steps starting from Garner's aldehyde and proceeds in 20% overall yield. Pd(0)-mediated intramolecular cyclisation and Ru-mediated cross-metathesis are the key reactions in this sequence. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:980 / 983
页数:4
相关论文
共 50 条
  • [21] 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
  • [22] Asymmetric synthesis of jaspine B (pachastrissamine) via an organocatalytic aldol reaction as key step
    Enders, Dieter
    Terteryan, Violeta
    Palecek, Jiri
    SYNTHESIS-STUTTGART, 2008, 14 SPEC. ISS. (14): : 2278 - 2282
  • [23] 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
  • [24] Stereoselective synthesis of jaspine B from D-xylose
    Liu, Jun
    Du, Yuguo
    Dong, Xiaomin
    Meng, Shucong
    Xiao, Junjun
    Cheng, Lijian
    CARBOHYDRATE RESEARCH, 2006, 341 (16) : 2653 - 2657
  • [25] Asymmetric synthesis of Pachastrissamine (Jaspine B) and its diastereomers via η3-allylpalladium intermediates
    Department of Chemistry, School of Chemical Technology, Aalto University, Kemistintie 1, FI-00076, Aalto, Finland
    Org. Biomol. Chem., 6 (1774-1783):
  • [26] Enantioselective Synthesis of Jaspine B (Pachastrissamine) and Its C-2 and/or C-3 Epimers
    Llaveria, Josep
    Diaz, Yolanda
    Isabel Matheu, M.
    Castillon, Sergio
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (08) : 1514 - 1519
  • [27] A common strategy for the stereoselective synthesis of anhydrophytosphingosine pachastrissamine (jaspine B) and N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine
    Rao, G. Srinivas
    Rao, B. Venkateswara
    TETRAHEDRON LETTERS, 2011, 52 (46) : 6076 - 6079
  • [28] Pachastrissamine (jaspine B) and its stereoisomers inhibit sphingosine kinases and atypical protein kinase C
    Yoshimitsu, Yuji
    Oishi, Shinya
    Miyagaki, Jun
    Inuki, Shinsuke
    Ohno, Hiroaki
    Fujii, Nobutaka
    BIOORGANIC & MEDICINAL CHEMISTRY, 2011, 19 (18) : 5402 - 5408
  • [29] Asymmetric synthesis of N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine, jaspine B (pachastrissamine), 2-epi-jaspine B, and deoxoprosophylline via lithium amide conjugate addition
    Abraham, Elin
    Brock, E. Anne
    Candela-Lena, Jose I.
    Davies, Stephen G.
    Georgiou, Matthew
    Nicholson, Rebecca L.
    Perkins, James H.
    Roberts, Paul M.
    Russell, Angela J.
    Sanchez-Fernandez, Elena M.
    Scott, Philip M.
    Smith, Andrew D.
    Thomson, James E.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (09) : 1665 - 1673
  • [30] Enantioselective Syntheses of Pachastrissamine and Jaspine A via Hydroxylactonization of a Chiral Epoxy Ester
    Urano, Hiroyuki
    Enomoto, Masaru
    Kuwahara, Shigefumi
    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2010, 74 (01) : 152 - 157