Chemoenzymatic synthesis of 2-brorno-6-hydroxy-3-methoxy-2-cyclohexen-1-one

被引：0
|
作者：
Karaaslan, Emine Ozgul [1 ]
Toka, Yasemin [1 ]
机构：
[1] Kirikkale Univ, Fac Arts & Sci, Dept Chem, TR-71400 Kirikkale, Turkey
来源：
TURKISH JOURNAL OF CHEMISTRY | 2007年 / 31卷 / 02期
关键词：
chemoenzymatic synthesis; cyclic polyoxo cyclohexenones; manganese (III) acetate; acetoxylation;
D O I：
暂无
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A chemoenzymatic synthesis of 2-bromo-6-hydroxy-3-methoxy-2-cyclohexen-1-one starting from cyclohexane-1,3-dione is reported. Manganese (III) acetate-mediated acetoxylation followed by the enzyme-mediated hydrolysis of alpha'-acetoxy enone affords hydroxy-enone 5 and enone 4 with high enantiomeric excesses in good yields.
引用
收藏
页码：149 / 153
页数：5
相关论文
共 35 条
  • [21] 3-Amino-1-methyl-1H-pyridin-2-one-Directed PcII Catalysis: C(sp3)-H Activated Diverse Arylation Reaction
    Pati, Tanmay K.
    Debnath, Sudipto
    Kundu, Mrinalkanti
    Khamrai, Uttam
    Maiti, Dilip K.
    ORGANIC LETTERS, 2018, 20 (13) : 4062 - 4066
  • [22] Protecting group free glycosylation: one-pot stereocontrolled access to 1,2-trans glycosides and (1→6)-linked disaccharides of 2-acetamido sugars
    Qiu, Xin
    Garden, Anna L.
    Fairbanks, Antony J.
    CHEMICAL SCIENCE, 2022, 13 (14) : 4122 - 4130
  • [23] Chemoenzymatic Synthesis of the New 3-((2,3-Diacetoxypropanoyl)oxy)propane-1,2-diyl Diacetate Using Immobilized Lipase B from Candida antarctica and Pyridinium Chlorochromate as an Oxidizing Agent
    Plata, Esteban
    Ruiz, Monica
    Ruiz, Jennifer
    Ortiz, Claudia
    Castillo, John J.
    Fernandez-Lafuente, Roberto
    INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2020, 21 (18) : 1 - 14
  • [24] Combination of Glycosyltransferases and a Glycosynthase in Sequential and One-Pot Reactions for the Synthesis of Type1 and Type2 N-Acetyllactosamine Oligomers
    Henze, Manja
    Schmidtke, Simon
    Hoffmann, Natalie
    Steffens, Hanna
    Pietruszka, Joerg
    Elling, Lothar
    CHEMCATCHEM, 2015, 7 (19) : 3131 - 3139
  • [25] Coupling biocatalysis and click chemistry: one-pot two-step convergent synthesis of enantioenriched 1,2,3-triazole-derived diols
    Cuetos, Anibal
    Bisogno, Fabricio R.
    Lavandera, Ivan
    Gotor, Vicente
    CHEMICAL COMMUNICATIONS, 2013, 49 (26) : 2625 - 2627
  • [26] Synthesis and pharmacological characterization of the selective GluK1 radioligand (S)-2-amino-3-(6[ 3H]-2,4-dioxo-3,4-dihydrothieno.3,2-d] pyrimidin1.2H)- yl) propanoic acid ([3H]-NF608)
    Alcaide, Anna
    Marconi, Laura
    Marek, Ales
    Haym, Isabell
    Nielsen, Birgitte
    Mollerud, Stine
    Jensen, Mikael
    Conti, Paola
    Pickering, Darryl S.
    Bunch, Lennart
    MEDCHEMCOMM, 2016, 7 (11) : 2136 - 2144
  • [27] Differences in Absorption and Metabolism between Structured 1,3-Oleate-2-palmitate Glycerol and 1-Oleate-2-palmitate-3-linoleate Glycerol on C57BL/6J Mice
    Wei, Teng
    Tan, Dengfeng
    Zhong, Shengyue
    Zhang, Hong
    Deng, Zeyuan
    Li, Jing
    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2023, 71 (49) : 19610 - 19621
  • [28] Diastereoselective One-Step Synthesis of 2-Keto-3-deoxy-D-glycero-D-galacto-nononic acid (KDN) Analogues as Templates for the Development of Influenza Drugs
    Laborda, Pedro
    Wang, Su-Yan
    Lu, Ai-Min
    He, Meng
    Duan, Xu-Chu
    Qian, Ying-Juan
    Jung, Yong-Sam
    Liu, Li
    Voglmeir, Josef
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (18) : 3120 - 3125
  • [29] Chemical synthesis of human milk oligosaccharides: lacto-N-neohexaose (Galβ1 → 4GlcNAcβ1→)2 3,6Galβ1→ 4Glc
    Bandara, Mithila D.
    Stine, Keith J.
    Demchenko, Alexei V.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (09) : 1747 - 1753
  • [30] N-(7-(1H-Imidazol-1-yl)-2,3-dioxo-6-(trifluoromethyl)-3,4-dihydroquinoxalin-1(2H)-yl)benzamide, a New Kainate Receptor Selective Antagonist and Analgesic: Synthesis, X-ray Crystallography, Structure-Affinity Relationships, and in Vitro and in Vivo Pharmacology
    Mollerud, Stine
    Hansen, Rie B.
    Pallesen, Jakob
    Temperini, Piero
    Pasini, Diletta
    Bornholt, Jan
    Nielsen, Birgitte
    Mamedova, Esmira
    Chalupnik, Paulina
    Paternain, Ana V.
    Lerma, Juan
    Diaz-delCastillo, Marta
    Andreasen, Jesper T.
    Frydenvang, Karla
    Kastrup, Jette S.
    Johansen, Tommy N.
    Pickering, Darryl S.
    ACS CHEMICAL NEUROSCIENCE, 2019, 10 (11): : 4685 - 4695
1234