Divergent synthesis of oxacyclophenylpropanoids from biomass-derived eugenol

被引：2
|
作者：
Li, Guohui [1 ]
Zhang, Qingqing [1 ]
Zhuang, Wenhao [1 ]
Cheng, Xi [1 ]
Jiang, Tao-Shan [1 ]
Cai, Yongping [1 ]
机构：
[1] Anhui Agr Univ, Sch Life Sci, Hefei 230036, Anhui, Peoples R China
来源：
TETRAHEDRON LETTERS | 2019年 / 60卷 / 22期
基金：
中国国家自然科学基金;
关键词：
Phenylpropanoids; DDQ; Palladium-catalyzed cyclization; RCM; RING-CLOSING METATHESIS; OXIDATIVE CYCLIZATION; COUMARIN DERIVATIVES; LIGNIN; BIOSYNTHESIS; CONSTITUENTS; EVOLUTION; ACCESS; TEA;
D O I：
10.1016/j.tetlet.2019.04.057
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A divergent synthesis of new oxacyclophenylpropanoids from the readily available and biomass-derived starting material eugenol is reported. The synthetic routes feature two important steps, including (i) DDQ-mediated selective oxidation of an allyl group and subsequent Claisen-rearrangement for the formation of key intermediates 1 and 11, and (ii) five-membered or six-membered ring formation via either palladium-catalyzed cyclization or ring-closing metathesis (RCM) strategies. (C) 2019 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1501 / 1504
页数：4
相关论文
共 50 条
  • [11] A divergent approach for the synthesis of (hydroxymethyl)furfural (HMF) from spent aromatic biomass-derived (chloromethyl)furfural (CMF) as a renewable feedstock
    Singh, Mangat
    Pandey, Nishant
    Mishra, Bhuwan B.
    RSC ADVANCES, 2020, 10 (73) : 45081 - 45089
  • [12] Synthesis of Renewable Lubricant Alkanes from Biomass-Derived Platform Chemicals
    Gu, Mengyuan
    Xia, Qineng
    Liu, Xiaohui
    Guo, Yong
    Wang, Yanqin
    CHEMSUSCHEM, 2017, 10 (20) : 4102 - 4108
  • [13] Synthesis gas production from steam gasification of biomass-derived oil
    Panigrahi, S
    Dalai, AK
    Chaudhari, ST
    Bakhshi, NN
    ENERGY & FUELS, 2003, 17 (03) : 637 - 642
  • [14] Synthesis of Renewable meta-Xylylenediamine from Biomass-Derived Furfural
    Scodeller, Ivan
    Mansouri, Samir
    Morvan, Didier
    Muller, Eric
    Vigier, Karine de Oliveira
    Wischert, Raphael
    Jerome, Francois
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (33) : 10510 - 10514
  • [15] Selective Synthesis of THF-Derived Amines from Biomass-Derived Carbonyl Compounds
    Jiang, Shi
    Ma, Changru
    Muller, Eric
    Pera-Titus, Marc
    Jerome, Francois
    Vigier, Karine De Oliveira
    ACS CATALYSIS, 2019, 9 (10): : 8893 - 8902
  • [16] A sustainable system for maleic acid synthesis from biomass-derived sugar
    Yu, Qiang
    Bai, Ruxue
    Wang, Fan
    Zhang, Qinghua
    Sun, Yongming
    Zhang, Yu
    Qin, Lei
    Wang, Zhongming
    Yuan, Zhenhong
    JOURNAL OF CHEMICAL TECHNOLOGY AND BIOTECHNOLOGY, 2020, 95 (03) : 751 - 757
  • [17] Biomass-derived plastic
    Furuki, J
    JOURNAL OF THE JAPANESE SOCIETY FOR FOOD SCIENCE AND TECHNOLOGY-NIPPON SHOKUHIN KAGAKU KOGAKU KAISHI, 2005, 52 (06): : 278 - 278
  • [18] BIOMASS-DERIVED POLYMERS
    Fisher, Charles H.
    CHEMICAL & ENGINEERING NEWS, 2008, 86 (45) : 3 - 3
  • [19] Synthesis and Kinetic Modeling of Biomass-Derived Renewable Polyesters
    Lomeli-Rodriguez, Monica
    Martin-Molina, Miguel
    Jimenez-Pardo, Maria
    Nasim-Afzal, Zahara
    Cauet, Solene I.
    Davies, Thomas E.
    Rivera-Toledo, Martin
    Lopez-Sanchez, Jose A.
    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2016, 54 (18) : 2876 - 2887
  • [20] Synthesis of Biomass-Derived Ethers for Use as Fuels and Lubricants
    Rorrer, Julie E.
    Bell, Alexis T.
    Toste, F. Dean
    CHEMSUSCHEM, 2019, 12 (13) : 2835 - 2858
12345