Novel, efficient and stereospecific synthesis of xylo-(2R,3S,4S)-phytosphingosine and threo-(2R,3R)-sphingosine

被引:22
|
作者
Raghavan, S [1 ]
Rajender, A [1 ]
Yadav, JS [1 ]
机构
[1] Indian Inst Chem Technol, Organ Div 1, Hyderabad 500007, Andhra Pradesh, India
关键词
D O I
10.1016/S0957-4166(03)00427-0
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The stereo- and regioselective elaboration of a bromohydrin from an olefinic precursor and Pummerer ene reaction for carbon-carbon bond formation are the key steps in a novel and flexible synthesis of xylo-phytosphingosine and threo-sphingosine. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2093 / 2099
页数:7
相关论文
共 50 条
  • [1] Novel, short, stereospecific synthesis of lyxo-(2R,3R,4R)-Phytosphingosine and erythro-(2R,3S)-sphingosine
    Raghavan, S
    Rajender, A
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (18): : 7094 - 7097
  • [2] 4-Formylazetidin-2-one as a useful building block for the formal synthesis of xylo-(2S,3R,4R)-phytosphingosine and threo-(2S,3S)-sphingosine
    Kale, Ajaykumar S.
    Sakle, Prathmesh S.
    Gumaste, Vikas K.
    Deshmukh, Abdul Rakeeb A. S.
    SYNTHESIS-STUTTGART, 2007, (17): : 2631 - 2636
  • [3] Stereoselective synthesis of (2R,3R) and (2R,3S)-3-hydroxyleucines
    Raghavan, S
    Tony, KA
    TETRAHEDRON LETTERS, 2004, 45 (12) : 2639 - 2641
  • [4] An efficient stereoselective and stereodivergent synthesis of (2R,3R)- and (2R,3S)-3-hydroxypipecolic acids
    Jourdant, A
    Zhu, JP
    TETRAHEDRON LETTERS, 2000, 41 (36) : 7033 - 7036
  • [5] An efficient asymmetric synthesis of (2S,3S)- and (2R,3R)-β-hydroxyornithine
    DeMong, DE
    Williams, RM
    TETRAHEDRON LETTERS, 2001, 42 (02) : 183 - 185
  • [6] Enantioselective synthesis of (2R,3R)- and (2S,3S)-β-hydroxyornithine
    Pandey, Satyendra Kumar
    Kumar, Pradeep
    TETRAHEDRON LETTERS, 2006, 47 (25) : 4167 - 4169
  • [7] Synthesis of (2R,3R)-erythro- and (2R,3S)-threo-fluoromalate using malic dehydrogenase;: Stereoselectivity of malic dehydrogenase
    Urbauer, JL
    Bradshaw, DE
    Cleland, WW
    BIOCHEMISTRY, 1998, 37 (51) : 18018 - 18025
  • [8] Stereospecific synthesis of the (2R,3S)- and (2R,3R)-3-amino-2-hydroxy-4-phenylbutanoic acids from D-glucono-δ-lactone
    Lee, Jin Hwan
    Kim, Jin Hyo
    Lee, Byong Won
    Seo, Woo Duck
    Yang, Min Suk
    Park, Ki Hun
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2006, 27 (08) : 1211 - 1218
  • [9] SYNTHESIS OF (2R,3R)-, (2S,3S)-, (2R,3S)- AND (2S,3R)-IMIDAZOLE GLYCEROL PHOSPHATES (IGP) - SUBSTRATES FOR IGP-DEHYDRATASE (IGPD)
    SAIKA, H
    FRUH, T
    IWASAKI, G
    KOIZUMI, S
    MORI, I
    HAYAKAWA, K
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (10) : 2129 - 2134
  • [10] Stereoselective synthesis of trans-(2R,3S)- and cis-(2R,3R)-disubstituted pyrrolidines
    Kim, YA
    Oh, SM
    Han, SY
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2001, 22 (03) : 327 - 329