DIASTEREOSELECTIVE CONJUGATE ADDITION APPROACH TO PICENADOL AND OXYGENATED ANALOGS

被引：0
|
作者：
MARTINELLI, MJ
PETERSON, BC
HUTCHISON, DR
机构：
来源：
HETEROCYCLES | 1993年 / 36卷 / 09期
关键词：
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Horner-Emmons-Wadsworth reaction with 1,3-dimethyl-4-piperidone in water afforded an exocyclic enone, with minimal deconjugation of the double bond. Copper catalyzed conjugate addition with an aryl Grignard reagent then afforded an adduct with high stereo control. Wolff-Kisch ner reduction and deprotection proceeded to provide picenadol (1) in excellent overall yield. Access to oxygenated analogues of picenadol was also accomplished with this approach.
引用
收藏
页码：2087 / 2097
页数：11
相关论文
共 50 条
  • [31] Chemo and diastereoselective conjugate addition of Grignard reagents on parthenin, a bioactive natural sesquiterpene lactone
    Kashanna, Jajula
    Jangili, Paramesh
    Kumar, Rathod Aravind
    Rao, Bethapudirr Rama
    TETRAHEDRON LETTERS, 2013, 54 (13) : 1634 - 1637
  • [32] Diastereoselective conjugate addition to (+)-camphorsulfonic acid derived nitroalkenes:: Synthesis of α-hydroxy and α-amino acids
    Barrett, AGM
    Braddock, DC
    Christian, PWN
    Pilipauskas, D
    White, AJP
    Williams, DJ
    JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (17): : 5818 - 5823
  • [33] Organocatalytic Enantio- and Diastereoselective Conjugate Addition to Nitroolefins: When β-Ketoamides Surpass β-Ketoesters
    Du, Haiying
    Rodriguez, Jean
    Bugaut, Xavier
    Constantieux, Thierry
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (27) : 8458 - 8466
  • [34] Diastereoselective conjugate addition of Grignard reagents to a homochiral fumaramide derived from Oppolzer's sultam
    Reid, GP
    Brear, KW
    Robins, DJ
    TETRAHEDRON-ASYMMETRY, 2004, 15 (05) : 793 - 801
  • [35] SYNTHESIS OF (-)-HELIOTRIDANE AND (-)-ISORETRONECANOL VIA DIASTEREOSELECTIVE CONJUGATE ADDITION OF ORGANOCUPRATES TO AN ENOATE DERIVING FROM PROLINE
    LECOZ, S
    MANN, A
    THAREAU, F
    TADDEI, M
    HETEROCYCLES, 1993, 36 (09) : 2073 - 2079
  • [36] CONJUGATE ADDITION OF ARYLACETONITRILES TO CINNAMIC ACID-DERIVATIVES - A CASE OF HIGH DIASTEREOSELECTIVE ASYMMETRIC PROTONATION
    VITEVA, L
    STEFANOVSKY, Y
    TETRAHEDRON LETTERS, 1989, 30 (34) : 4565 - 4568
  • [37] Diastereoselective conjugate addition of cyanide to α,β-unsaturated oxazolidinones:: Enantioselective synthesis of ent-pregabalin and baclofen
    Armstrong, Alan
    Convine, Nicola J.
    Popkin, Matthew E.
    SYNLETT, 2006, (10) : 1589 - 1591
  • [38] CONJUGATE ADDITION TO THIIN-4-ONES - A NOVEL ROUTE TO THIATHROMBOXANE ANALOGS
    LANE, S
    TAYLOR, RJK
    TETRAHEDRON LETTERS, 1985, 26 (23) : 2821 - 2824
  • [39] Asymmetric and Diastereoselective Conjugate Addition Reactions: C-C Bond Formation at Large Scale
    Howell, Gareth P.
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2012, 16 (07) : 1258 - 1272
  • [40] Copper(I) mediated highly diastereoselective conjugate addition of Grignard reagents to 2-silyloxycyclopentenecarboxylates
    Dambrin, V
    Villieras, M
    Moreau, C
    Amri, H
    Toupet, L
    Villieras, J
    TETRAHEDRON LETTERS, 1996, 37 (35) : 6323 - 6326
12345