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
  • [41] Diastereoselective synthesis of lortalamine analogs
    Biala, J
    Czarnocki, Z
    Maurin, JK
    TETRAHEDRON-ASYMMETRY, 2002, 13 (10) : 1021 - 1023
  • [42] A CONJUGATE ADDITION - RADICAL CYCLIZATION APPROACH TO SESQUITERPENE PHENOLS
    CROMBIE, BS
    REDHOUSE, AD
    SMITH, C
    WALLACE, TW
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (04) : 403 - 404
  • [43] Highly diastereoselective conjugate addition of carbon nucleophiles to a chiral oxygenated alpha,beta-unsaturated delta-lactone. A straightforward synthesis of functionalized branched-chain L-sugars
    Herradon, B
    Fenude, E
    Bao, R
    Valverde, S
    JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (03): : 1143 - 1147
  • [44] Domino Asymmetric Conjugate Addition-Conjugate Addition
    Germain, Nicolas
    Schlaefli, Doriane
    Chellat, Mathieu
    Rosset, Stephane
    Alexakis, Alexandre
    ORGANIC LETTERS, 2014, 16 (07) : 2006 - 2009
  • [45] Trialkylsilyl triflates -: Practical diastereoselective catalysts in conjugate addition reaction of silyl ketene acetals and α,β-unsaturated ketones
    Michalak, K
    Wicha, J
    POLISH JOURNAL OF CHEMISTRY, 2004, 78 (02) : 205 - 215
  • [46] Asymmetric Catalytic Enantio- and Diastereoselective Boron Conjugate Addition Reactions of α-Functionalized α,β-Unsaturated Carbonyl Substrates
    Xie, Jian-Bo
    Lin, Siqi
    Qiao, Shuo
    Li, Guigen
    ORGANIC LETTERS, 2016, 18 (15) : 3926 - 3929
  • [47] Total Synthesis of Gelsedilam by Means of a Thiol-Mediated Diastereoselective Conjugate Addition-Aldol Reaction
    Huang, You-Ming
    Liu, Yang
    Zheng, Chang-Wu
    Jin, Qiao-Wen
    Pan, Lu
    Pan, Ren-Ming
    Liu, Jun
    Zhao, Gang
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (51) : 18339 - 18342
  • [48] A new route to keto and alkyl derivatives of (R)-carvone via diastereoselective conjugate addition of nitronate ions
    Costa, Jeronimo S.
    Freire, Bruno S.
    Moura, Andre L. S.
    Pereira, Vera L. Patrocinio
    JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2006, 17 (07) : 1229 - 1232
  • [49] Highly diastereoselective conjugate addition to alkylidene Bis(Sulfoxides):: Asymmetric synthesis of (+)-erythro-roccellic acid
    Brebion, F
    Delouvrié, B
    Nájera, F
    Fensterbank, L
    Malacria, M
    Vaissermann, J
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (43) : 5342 - 5345
  • [50] Diastereoselective 1,4-Conjugate Addition of Alkyl Cuprates to Methyl Cyclopent-1-enecarboxylates
    Karlsson, Staffan
    Cornwall, Philip
    Cruz, Angele
    Ponten, Fritiof
    Friden-Saxin, Maria
    Turner, Andrew
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2018, 22 (03) : 337 - 343
12345