Snythesis of Δ12,14-15-deoxy-PG-J1 methyl ester and epi-Δ12-15-deoxy-PG-J1

被引:34
作者
Iqbal, M [1 ]
Li, YF [1 ]
Evans, P [1 ]
机构
[1] Univ Liverpool, Dept Chem, Liverpool L69 7ZD, Merseyside, England
关键词
Delta(12,14)-15-deoxy-PGJ(1); conjugate addition-Peterson olefination; epi-Delta(12)-15-deoxy-PG(1); cross-conjugated cyclopenteone;
D O I
10.1016/j.tet.2004.01.048
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of racemic Delta(12,14)-15-deoxy-PG-J(1) is readily achieved in six steps employing as the key transformation a one-pot conjugate addition-Peterson olefination sequence using exo-2-trimethylsilyl-3a,4,7,7a-tetrahydro-4,7-methanoinden-1-one. Additionally a Noyori-type three-component coupling approach is employed for the synthesis of enantioenriched epi-Delta(12)-15-deoxy-PG-J(1) from 4(S)-tert-butyldimethylsilyloxycyclopent-2-enone. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2531 / 2538
页数:8
相关论文
共 33 条
  • [1] A novel approach to bis-isoxazolines using a latent form of cyclopentadienone
    Basra, SK
    Drew, MGB
    Mann, J
    Kane, PD
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (21): : 3592 - 3598
  • [2] MICROWAVE-ASSISTED ORGANIC-REACTIONS
    CADDICK, S
    [J]. TETRAHEDRON, 1995, 51 (38) : 10403 - 10432
  • [3] Formation of reactive cyclopentenone compounds in vivo as products of the isoprostane pathway
    Chen, Y
    Morrow, JD
    Roberts, LJ
    [J]. JOURNAL OF BIOLOGICAL CHEMISTRY, 1999, 274 (16) : 10863 - 10868
  • [4] SYNTHESIS OF THERAPEUTICALLY USEFUL PROSTAGLANDIN AND PROSTACYCLIN ANALOGS
    COLLINS, PW
    DJURIC, SW
    [J]. CHEMICAL REVIEWS, 1993, 93 (04) : 1533 - 1564
  • [5] Human colorectal cancer cells efficiently conjugate the cyclopentenone prostaglandin, prostaglandin J2, to glutathione
    Cox, B
    Murphey, LJ
    Zackert, WE
    Chinery, R
    Graves-Deal, R
    Boutaud, O
    Oates, JA
    Coffey, RJ
    Morrow, JD
    [J]. BIOCHIMICA ET BIOPHYSICA ACTA-MOLECULAR AND CELL BIOLOGY OF LIPIDS, 2002, 1584 (01): : 37 - 45
  • [6] 15-DEOXY-DELTA(12,14)-PROSTAGLANDIN J(2) IS A LIGAND FOR THE ADIPOCYTE DETERMINATION FACTOR PPAR-GAMMA
    FORMAN, BM
    TONTONOZ, P
    CHEN, J
    BRUN, RP
    SPIEGELMAN, BM
    EVANS, RM
    [J]. CELL, 1995, 83 (05) : 803 - 812
  • [7] Antitumor activity, optimum administration method and pharmacokinetics of 13,14-dihydro-15-deoxy-Δ7-prostaglandin A1 methyl ester (TEI-9826) integrated in lipid microspheres (Lipo TEI-9826)
    Fukushima, S
    Takeuchi, Y
    Kishimoto, S
    Yamashita, S
    Uetsuki, K
    Shirakawa, S
    Suzuki, M
    Furuta, K
    Noyori, R
    Sasaki, H
    Kikuchi, Y
    Kita, T
    Yamori, T
    Sawada, J
    Kojima, M
    Hazato, A
    Kurozumi, S
    Fukushima, M
    [J]. ANTI-CANCER DRUGS, 2001, 12 (03) : 221 - 234
  • [8] Prostaglandins and leukotrienes: Advances in eicosanoid biology
    Funk, CD
    [J]. SCIENCE, 2001, 294 (5548) : 1871 - 1875
  • [9] FACILE RETRO DIELS-ALDER REACTION OF A PENTAMETHYLTRICYCLO[5.2.1.0/2,6]DECENONE DERIVATIVE - SYNTHESIS OF (+)-15(S)-PROSTAGLANDIN-A2
    GRIECO, PA
    ABOOD, N
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (05) : 410 - 412
  • [10] Conjugate addition-Peterson olefination reactions: expedient routes to cross conjugated dienones
    Iqbal, M
    Evans, P
    [J]. TETRAHEDRON LETTERS, 2003, 44 (30) : 5741 - 5745