Synthesis of the human aldose reductase inhibitor rubrolide L

被引:46
作者
Boukouvalas, John [1 ]
McCann, Lucas C. [1 ]
机构
[1] Univ Laval, Dept Chim, Quebec City, PQ G1V 0A6, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
Diabetes; Selective bromination; Suzuki-Miyaura cross-coupling; Vinylogous aldol condensation; EFFICIENT TOTAL-SYNTHESIS; CROSS-COUPLING REACTIONS; SUBSTITUTED BUTENOLIDES; SELECTIVE SYNTHESIS; NATURAL-PRODUCTS; FACILE SYNTHESIS; ACID; ARYL; ACCESS; STEREOCHEMISTRY;
D O I
10.1016/j.tetlet.2010.06.129
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first synthesis of rubrolide L, a marine ascidian butenolide and a potent inhibitor of human aldose reductase, has been achieved by two tactically distinct pathways in 4-5 steps and 37-42% overall yield from commercially available 3-chlorotetronic acid. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4636 / 4639
页数:4
相关论文
共 63 条
  • [1] Design and synthesis of N-( 3,5-difluoro-4-hydroxyphenyl) benzenesulfonamides as aldose reductase inhibitors
    Alexiou, Polyxeni
    Nicolaou, Ioannis
    Stefek, Milan
    Kristl, Albin
    Demopoulos, Vassilis J.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (07) : 3926 - 3932
  • [2] Aldose Reductase Enzyme and its Implication to Major Health Problems of the 21st Century
    Alexiou, Polyxeni
    Pegklidou, Kyriaki
    Chatzopoulou, Maria
    Nicolaou, Ioannis
    Demopoulos, Vassilis J.
    [J]. CURRENT MEDICINAL CHEMISTRY, 2009, 16 (06) : 734 - 752
  • [3] Mucochloric acid:: A useful synthon for the selective synthesis of 4-aryl-3chloro-2(5H)-furanones, (Z)-4-aryl-5-[1-(aryl)methylidenel-3-chloro-2(5H)furanones and 3,4-diaryl-2(5H)-furanones
    Bellina, F
    Anselmi, C
    Martina, F
    Rossi, R
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (12) : 2290 - 2302
  • [4] Total synthesis of rubrolide M and some of its unnatural congeners
    Bellina, F
    Anselmi, C
    Rossi, R
    [J]. TETRAHEDRON LETTERS, 2002, 43 (11) : 2023 - 2027
  • [5] Selective synthesis of (Z)-4-aryl-5-[1-(aryl)methylidene]-3-bromo-2(5H)-furanones
    Bellina, F
    Anselmi, C
    Viel, S
    Mannina, L
    Rossi, R
    [J]. TETRAHEDRON, 2001, 57 (50) : 9997 - 10007
  • [6] An Economical Access to 3,4-Diaryl-2(5H)-furanones and 4-Aryl-6-methyl-2(2H)-pyranones by Pd-Catalyzed Suzuki-Type Arylation of 3-Aryl-4-tosyloxy-2(5H)-furanones and 6-Methyl-4-tosyloxy-2(2H)-pyranones, Respectively
    Bellina, Fabio
    Marchetti, Chiara
    Rossi, Renzo
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (27) : 4685 - 4690
  • [7] Short and efficient synthesis of cadiolide B
    Boukouvalas, J
    Pouliot, M
    [J]. SYNLETT, 2005, (02) : 343 - 345
  • [8] Facile access to 4-aryl-2(5H)-furanones by Suzuki cross coupling:: Efficient synthesis of rubrolides C and E
    Boukouvalas, J
    Lachance, N
    Ouellet, M
    Trudeau, M
    [J]. TETRAHEDRON LETTERS, 1998, 39 (42) : 7665 - 7668
  • [9] Total synthesis of (+)-dysidiolide
    Boukouvalas, J
    Cheng, YX
    Robichaud, J
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (02) : 228 - 229
  • [10] AN EFFICIENT TOTAL SYNTHESIS OF NEOPATULIN
    BOUKOUVALAS, J
    MALTAIS, F
    [J]. TETRAHEDRON LETTERS, 1994, 35 (32) : 5769 - 5770