Recent chemoenzymatic total syntheses of natural and unnatural products: Codeine, balanol, pancratistatin, and oseltamivir

被引:24
|
作者
Hudlicky, Tomas [1 ,2 ]
机构
[1] Brock Univ, Dept Chem, St Catharines, ON L2S 3A1, Canada
[2] Brock Univ, Ctr Biotechnol, St Catharines, ON L2S 3A1, Canada
基金
加拿大自然科学与工程研究理事会; 加拿大创新基金会;
关键词
balanol; chemoenzymatic synthesis; codeine; oseltamivir; pancratistatin; Tamiflu; toluene-dioxygenase; ENANTIOSELECTIVE TOTAL-SYNTHESIS; RADICAL CYCLIZATION APPROACH; FORMAL TOTAL-SYNTHESIS; ENZYMATIC DIHYDROXYLATION; RING CONSTRUCTION; BURGESS REAGENT; CHIRAL VERSION; MORPHINE; (-)-MORPHINE; (-)-GALANTHAMINE;
D O I
10.1351/PAC-CON-09-10-07
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Presented here is a short summary of the recent accomplishments in total synthesis in our laboratories. In particular, recent generations of the syntheses of pancratistatin derivatives, codeine, balanol, and oseltamivir (Tamiflu) are described in relation to their common chemoenzymatic origin in toluene-dioxygenase-mediated dioxygenation of aromatic substrates. Perspectives and projections are discussed in the conclusion.
引用
收藏
页码:1785 / 1796
页数:12
相关论文
共 50 条
  • [2] Chemoenzymatic enantiodivergent total syntheses of (+)- and (-)-codeine
    Leisch, Hannes
    Omori, Alvaro T.
    Finn, Kevin J.
    Gilmet, Jacqueline
    Bissett, Tyler
    Ilceski, David
    Hudlicky, Tomas
    TETRAHEDRON, 2009, 65 (47) : 9862 - 9875
  • [3] Chemoenzymatic Total Synthesis of Natural Products
    Chakrabarty, Suman
    Romero, Evan O.
    Pyser, Joshua B.
    Yazarians, Jessica A.
    Narayan, Alison R. H.
    ACCOUNTS OF CHEMICAL RESEARCH, 2021, 54 (06) : 1374 - 1384
  • [4] Recent total syntheses of anthraquinone-based natural products
    Gartman, Jackson A.
    Tambar, Uttam K.
    TETRAHEDRON, 2022, 105
  • [5] Recent advances in total syntheses of complex dimeric natural products
    Sun, Jiawei
    Yang, He
    Tang, Wenjun
    CHEMICAL SOCIETY REVIEWS, 2021, 50 (04) : 2320 - 2336
  • [6] Meroterpenoid natural products fromStreptomycesbacteria - the evolution of chemoenzymatic syntheses
    Murray, Lauren A. M.
    McKinnie, Shaun M. K.
    Moore, Bradley S.
    George, Jonathan H.
    NATURAL PRODUCT REPORTS, 2020, 37 (10) : 1334 - 1366
  • [7] Chemoenzymatic total synthesis of cryptocaryalactone natural products
    Reddy, Yarram Narasimha
    Kumari, Tenkayala Navya
    Thota, Pradeepkumar
    Jyothi, Perla
    Gupta, Ajay Kumar
    TETRAHEDRON LETTERS, 2018, 59 (02) : 160 - 162
  • [8] Recent strategies and tactics for the enantioselective total syntheses of cyclolignan natural products
    Reynolds, Rebekah G.
    Nguyen, Huong Quynh Anh
    Reddel, Jordan C. T.
    Thomson, Regan J.
    NATURAL PRODUCT REPORTS, 2022, 39 (03) : 670 - 702
  • [9] Recent advances in total syntheses of natural products containing the benzocycloheptane motif
    Fan, Jian-Hong
    Hu, Ya-Jian
    Li, Li-Xuan
    Wang, Jing-Jing
    Li, Shao-Ping
    Zhao, Jing
    Li, Chuang-Chuang
    NATURAL PRODUCT REPORTS, 2021, 38 (10) : 1821 - 1851
  • [10] Recent advances in the total syntheses of oxazole-containing natural products
    Yeh, VSC
    TETRAHEDRON, 2004, 60 (52) : 11995 - 12042