Jaspine B (pachastrissamine) and 2-epi-jaspine B:: synthesis and structural assignment

被引:59
作者
Abraham, Elin [1 ]
Davies, Stephen G. [1 ]
Roberts, Paul M. [1 ]
Russell, Angela J. [1 ]
Thomson, James E. [1 ]
机构
[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England
关键词
D O I
10.1016/j.tetasy.2008.04.017
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Jaspine B (pachastrissamine), which was isolated in 2002 is a naturally occurring anhydrophytosphingosine which displays polutent biological activity, and as such has attracted much attention from synthetic chemists in recent years, with 14 syntheses reported, to date. This review delineates the isolation of jaspine B, and laboratory total syntheses of jaspine B, 2-epi-jaspine B and analogues, which serves to confirm their structure and stereochemistry. (C) 2008 Elsevier Ltd. All rights reserved.
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收藏
页码:1027 / 1047
页数:21
相关论文
共 60 条
  • [1] Asymmetric synthesis of vicinal amino alcohols: xestoaminol C, sphinganine and sphingosine
    Abraham, Elin
    Davies, Stephen G.
    Millican, Nicholas L.
    Nicholson, Rebecca L.
    Roberts, Paul M.
    Smith, Andrew D.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (09) : 1655 - 1664
  • [2] 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.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (09) : 1665 - 1673
  • [3] Asymmetric synthesis of N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine, jaspine B (pachastrissamine) and its C(2)-epimer
    Abraham, Elin
    Candela-Lena, Jose I.
    Davies, Stephen G.
    Georgiou, Matthew
    Nicholson, Rebecca L.
    Roberts, Paul M.
    Russell, Angela J.
    Sanchez-Fernandez, Elena M.
    Smith, Andrew D.
    Thomson, James E.
    [J]. TETRAHEDRON-ASYMMETRY, 2007, 18 (21) : 2510 - 2513
  • [4] Ariga T, 1998, J LIPID RES, V39, P1
  • [5] NUCLEOPHILIC DISPLACEMENT OF AROMATIC NITRO-GROUPS
    BECK, JR
    [J]. TETRAHEDRON, 1978, 34 (14) : 2057 - 2068
  • [6] REGIOSPECIFICITY IN NUCLEOPHILIC DISPLACEMENT OF AROMATIC NITRO-GROUPS
    BENEDETTI, F
    MARSHALL, DR
    STIRLING, CJM
    LENG, JL
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (16) : 918 - 919
  • [7] Total synthesis of cytotoxic anhydrophytosphingosine pachastrissamine (Jaspine B)
    Bhaket, P
    Morris, K
    Stauffer, CS
    Datta, A
    [J]. ORGANIC LETTERS, 2005, 7 (05) : 875 - 876
  • [8] Complex peptidyl nucleoside antibiotics: Efficient syntheses of the glycosyl nucleoside amino acid cores
    Bhaket, P
    Stauffer, CS
    Datta, A
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (25) : 8594 - 8601
  • [9] BIRK R, 1993, LIEBIGS ANN CHEM, P71
  • [10] ASYMMETRIC-SYNTHESIS OF BETA-AMINO-ALPHA-HYDROXY ACIDS VIA DIASTEREOSELECTIVE HYDROXYLATION OF HOMOCHIRAL BETA-AMINO ENOLATES
    BUNNAGE, ME
    CHERNEGA, AN
    DAVIES, SG
    GOODWIN, CJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (17): : 2373 - 2384