Stereoselective synthesis of cytotoxic anhydrophytosphingosine pachastrissamine (Jaspine B) from D-xylose

被引：57
|
作者：
Du, YG [1 ]
Liu, J
Linhardt, RJ
机构：
[1] Chinese Acad Sci, Ecoenvironm Sci Res Ctr, State Key Lab Environm Chem & Ecotoxicol, Beijing 100085, Peoples R China
[2] Rensselaer Polytech Inst, Dept Chem, Troy, NY 12180 USA
[3] Rensselaer Polytech Inst, Dept Biol, Troy, NY 12180 USA
[4] Rensselaer Polytech Inst, Dept Chem & Biol Engn, Troy, NY 12180 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 03期
关键词：
D O I：
10.1021/jo051644y
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first naturally occurring anhydrophytosphingosine, pachastrissamine (jaspine B), a marine compound cytotoxic toward P388, A549, HT29, and MEL28 cell lines at IC50 = 0.01 μg/mL level, has been stereoselectively synthesized from D-xylose in 10 linear steps with 25.7% overall yield. © 2006 American Chemical Society.
引用
收藏
页码：1251 / 1253
页数：3
相关论文
共 50 条
  • [21] Stereoselective total synthesis of Jaspine B (Pachastrissamine) utilizing iodocyclization and an investigation of its cytotoxic activity (vol 24, pg 903, 2013)
    Ghosal, Partha
    Ajay, Sama
    Meena, Sanjeev
    Sinha, Sudhir
    Shaw, Arun K.
    TETRAHEDRON-ASYMMETRY, 2013, 24 (24) : 1625 - 1625
  • [22] Stereoselective synthesis of new higher carbon sugars from D-xylose
    Liu, HM
    Zou, DP
    Zhang, FY
    Zhu, WG
    Peng, T
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (10) : 2103 - 2106
  • [23] Concise synthesis of truncated pachastrissamine (jaspine B) and its enantiomer
    Chandrasekhar, S.
    Tiwari, Bhoopendra
    Prakash, S. Jaya
    ARKIVOC, 2006, : 155 - 161
  • [24] Synthesis of (+)-azafagomine from D-xylose
    Ernholt, BV
    Thomsen, IB
    Jensen, KB
    Bols, M
    SYNLETT, 1999, (06) : 701 - 704
  • [25] A synthesis of (+)-cyclophellitol from D-xylose
    Ziegler, FE
    Wang, YZ
    JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (03): : 426 - 427
  • [26] Synthesis and biological properties of Pachastrissamine ( jaspine B) and diastereoisomeric jaspines
    Canals, Daniel
    Mormeneo, David
    Fabrias, Gemma
    Llebaria, Amadeu
    Casas, Josefina
    Delgado, Antonio
    BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (01) : 235 - 241
  • [27] SYNTHESIS OF STREPTOLIDINE FROM D-XYLOSE
    KUSUMOTO, S
    TSUJI, S
    SHIMA, K
    SHIBA, T
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1976, 49 (12) : 3611 - 3614
  • [28] Stereoselective model synthesis of the optically active olivil type of lignan from D-xylose
    Yamauchi, S
    Kinoshita, Y
    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2000, 64 (08) : 1563 - 1571
  • [29] Total synthesis of (-)-ent-pachastrissamine (ent-Jaspine B)
    Prasad, Kavirayani R.
    Penchalaiah, Kamala
    TETRAHEDRON-ASYMMETRY, 2011, 22 (13) : 1400 - 1403
  • [30] 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
12345