Combining two-directional synthesis and tandem reactions. Part 4: A concise approach to the spirocyclic core of halichlorine and the pinnaic acids

被引:36
作者
Arini, LG
Szeto, P
Hughes, DL
Stockman, RA [1 ]
机构
[1] Univ E Anglia, Sch Chem Sci & Pharm, Norwich NR4 7TJ, Norfolk, England
[2] GlaxoSmithKline, Stevenage SG1 2NY, Herts, England
[3] Univ E Anglia, Sch Chem Sci & Pharm, Xray Crystallog Unit, Norwich NR4 7TJ, Norfolk, England
基金
英国工程与自然科学研究理事会;
关键词
halichlorine; pinnaic acid; cycloaddition; tandem reaction; two directional;
D O I
10.1016/j.tetlet.2004.09.058
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A synthesis of the spirocyclic core structure of halichlorine, an inhibitor of the induced expression of VCAM-1 and the pinnaic acids, inhibitors of PLA(2), is presented. A two-directional strategy is employed, in conjunction with a tandem oxime formation/Michael addition/cycloaddition to form the key azaspirocyclic skeleton in a very direct manner. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8371 / 8374
页数:4
相关论文
共 49 条
  • [1] Absolute stereochemistry of halichlorine; A potent inhibitor of VCAM-1 induction
    Arimoto, H
    Hayakawa, I
    Kuramoto, M
    Uemura, D
    [J]. TETRAHEDRON LETTERS, 1998, 39 (08) : 861 - 862
  • [2] Synthesis of pinnaic acid; Asymmetric construction of spirocyclic core
    Arimoto, H
    Asano, S
    Uemura, D
    [J]. TETRAHEDRON LETTERS, 1999, 40 (18) : 3583 - 3586
  • [3] THROMBOXANE-A2 - ITS GENERATION AND ROLE IN PLATELET ACTIVATION
    ARITA, H
    NAKANO, T
    HANASAKI, K
    [J]. PROGRESS IN LIPID RESEARCH, 1989, 28 (04) : 273 - 301
  • [4] X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .33. GENERATION OF NITRONES FROM OXIMES - TANDEM MICHAEL ADDITION-1,3-DIPOLAR CYCLOADDITION REACTIONS - CLASS-2 PROCESSES IN WHICH THE DIPOLAROPHILE IS LOCATED WITHIN THE OXIME
    ARMSTRONG, P
    GRIGG, R
    HEANEY, F
    SURENDRAKUMAR, S
    WARNOCK, WJ
    [J]. TETRAHEDRON, 1991, 47 (25) : 4495 - 4518
  • [5] Carson MW, 2001, ANGEW CHEM INT EDIT, V40, P4450, DOI 10.1002/1521-3773(20011203)40:23<4450::AID-ANIE4450>3.0.CO
  • [6] 2-M
  • [7] Carson MW, 2001, ANGEW CHEM INT EDIT, V40, P4453, DOI 10.1002/1521-3773(20011203)40:23<4453::AID-ANIE4453>3.0.CO
  • [8] 2-4
  • [9] Pinnaic acid and tauropinnaic acid: Two novel fatty acids composing a 6-Azaspiro[4.5]decane unit from the Okinawan bivalve Pinna muricata
    Chou, T
    Kuramoto, M
    Otani, Y
    Shikano, M
    Yazawa, K
    Uemura, D
    [J]. TETRAHEDRON LETTERS, 1996, 37 (22) : 3871 - 3874
  • [10] A new route to 2-spiropiperidines
    Ciblat, S
    Canet, JL
    Troin, Y
    [J]. TETRAHEDRON LETTERS, 2001, 42 (29) : 4815 - 4817