Enantioselective access to a versatile 4-oxazolidinonecarbaldehyde and application to the synthesis of a cytotoxic jaspine B truncated analogue

被引：32
|
作者：
Genisson, Yves [1 ]
Lamande, Lydia
Salma, Yahya
Andrieu-Abadie, Nathalie
Andre, Chantal
Baltas, Michel
机构：
[1] Univ Toulouse 3, LSPCMIB, UMR 5068, F-31062 Toulouse 9, France
[2] Inst Med Mol Rangueil, INSERM, U858, F-31432 Toulouse, France
来源：
TETRAHEDRON-ASYMMETRY | 2007年 / 18卷 / 07期
关键词：
D O I：
10.1016/j.tetasy.2007.03.029
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The preparation of the versatile aldehyde 15 via a concise route based on a formal anti-asymmetric aminohydroxylation and its use in a 5-step synthesis of a cytotoxic C-12 analogue of the natural anhydrophytosphingosine jaspine B is presented. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码：857 / 864
页数：8
相关论文
共 12 条
  • [1] Enantioselective Stereodivergent Synthesis of Jaspine B and 4-epi-Jaspine B from Axially Chiral Allenols
    Alnazer, Heba
    Castellan, Tessa
    Salma, Yahya
    Genisson, Yves
    Ballereau, Stephanie
    SYNLETT, 2019, 30 (02) : 185 - 188
  • [2] Total synthesis of (-)-jaspine B and its 4-epi-analogue from D-xylose
    Martinkova, Miroslava
    Mezeiova, Eva
    Gonda, Jozef
    Jackova, Dominika
    Pomikalova, Kvetoslava
    TETRAHEDRON-ASYMMETRY, 2014, 25 (09) : 750 - 766
  • [3] DEVELOPMENT OF A VERSATILE METHODOLOGY FOR THE SYNTHESIS OF D4 SYMMETRICAL PORPHYRINS AND THEIR APPLICATION TO ENANTIOSELECTIVE CATALYSIS
    CAMPBELL, LA
    BARRY, JF
    KODADEK, TJ
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 207 : 442 - ORGN
  • [4] An enantioselective synthesis of differentially protected erythro-α,β-diamino acids and its application to the synthesis of an analogue of rhodopeptin B5
    Durham, TB
    Miller, MJ
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (01): : 35 - 42
  • [5] Substrate and stereocontrolled iodocycloetherification of highly functionalized enantiomerically pure allylic alcohols: application to synthesis of cytotoxic 2-epi jaspine B and its biological evaluation
    Kundooru, Somireddy
    Das, Pintu
    Meena, Sanjeev
    Kumar, Vikash
    Siddiqi, Mohammad Imran
    Datta, Dipak
    Shaw, Arun K.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (30) : 8241 - 8250
  • [6] A Short Access to 3-Hydroxy-4-hydroxymethyltetrahydrofurans: Application to the Total Synthesis of Amphiasterin B4
    Salim, Hani
    Piva, Olivier
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (05): : 2257 - 2260
  • [7] Highly stereoselective construction of 4,6-cis-substituted quinolizidine ring core:: An application to enantioselective total synthesis of the marine alkaloid clavepictines A, B and pictamine
    Toyooka, N
    Yotsui, Y
    Yoshida, Y
    Momose, T
    Nemoto, H
    TETRAHEDRON, 1999, 55 (52) : 15209 - 15224
  • [8] Construction of 4a,8a-cis-octahydroquinolin-7-one core using an intramolecular aldol type of cyclization:: An application to enantioselective total synthesis of lepadin B
    Toyooka, N
    Okumura, M
    Takahata, H
    Nemoto, H
    TETRAHEDRON, 1999, 55 (35) : 10673 - 10684
  • [9] Versatile deep eutectic solvent assisted synthesis of ZnB2O4 (B = Al, Co, Cr) spinels: The effect of B site variants for comparing the bifunctional electrochemical sensing application
    Baby, Jeena N. N.
    Sriram, Balasubramanian
    Wang, Sea-Fue
    George, Mary
    CHEMICAL ENGINEERING JOURNAL, 2022, 435
  • [10] First enantioselective synthesis of (+)-(3R,3aS,6aS)-3-hydroxy-3,3a,4,6a-tetrahydrocyclopenta[b]furan-2-one -: a versatile chiral heterocyclic building block
    Kudis, S
    Helmchen, G
    TETRAHEDRON, 1998, 54 (35) : 10449 - 10456
12