Total synthesis of atorvastatin via a late-stage, regioselective 1,3-dipolar munchnone cycloaddition

被引:20
|
作者
Lopchuk, Justin M. [1 ]
Gribble, Gordon W. [1 ]
机构
[1] Dartmouth Coll, Dept Chem, Hanover, NH 03755 USA
关键词
Munchnone; 1,3-Dipolar cycloaddition; Atorvastatin; Pyrrole; Mesoionic; HMG-COA REDUCTASE; MULTICOMPONENT SYNTHESIS; CARBON-MONOXIDE; IMIDAZOLINES; DERIVATIVES; INHIBITORS; PYRROLES; IMINES;
D O I
10.1016/j.tetlet.2014.12.104
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Atorvastatin was prepared in seven steps from commercially available 4-fluorophenylacetic acid. The key 1,3-dipolar cycloaddition was conducted regioselectively using a complex munchnone which was prepared in five steps on decagram scale. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3208 / 3211
页数:4
相关论文
共 50 条
  • [41] Microscale synthesis of a diphenylisoxazoline by a 1,3-dipolar cycloaddition
    Martin, WB
    Kateley, LJ
    Wiser, DC
    Brummond, CA
    JOURNAL OF CHEMICAL EDUCATION, 2002, 79 (02) : 225 - 227
  • [43] Synthesis of functionalized sulfonamides via 1,3-dipolar cycloaddition of pentafluorophenyl vinylsulfonate
    Caddick, S
    Bush, HD
    ORGANIC LETTERS, 2003, 5 (14) : 2489 - 2492
  • [44] A regioselective 1,3-dipolar cycloaddition for the synthesis of novel spiro-chromene thiadiazole derivatives
    Zghab, Imen
    Trimeche, Belsem
    Touboul, David
    Ben Jannet, Hichem
    COMPTES RENDUS CHIMIE, 2014, 17 (02) : 171 - 178
  • [45] Synthesis of Spirocyclic and Tricyclic Isoxazoline via 1,3-Dipolar Cycloaddition Reactions
    Gul, Melek
    Tutar, Ahmet
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2014, 51 (02) : 327 - 335
  • [46] A NEW SYNTHESIS OF (D,L)-MUSCARONE VIA 1,3-DIPOLAR CYCLOADDITION
    DEMICHELI, C
    DEAMICI, M
    SCALFI, M
    FARMACO-EDIZIONE SCIENTIFICA, 1984, 39 (06): : 487 - 492
  • [47] Synthesis of potentially photoactivatable cournarin derivatives via a 1,3-dipolar cycloaddition
    Chenot, Elodie-Denise
    Rodriguez-Dominguez, Juan Carlos
    Hannewald, Paul
    Comel, Alain
    Kirsch, Gilbert
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2008, 45 (05) : 1429 - 1435
  • [48] Synthesis of new β- and γ-aminopyrrolidinephosphonates via 1,3-dipolar cycloaddition of substituted vinylphosphonates
    Rabasso, Nicolas
    Fadel, Antoine
    TETRAHEDRON LETTERS, 2010, 51 (01) : 60 - 63
  • [49] Diastereoselective Synthesis of Nicotine Derivatives via 1,3-Dipolar Cycloaddition Reactions
    Ghandi, Mehdi
    Taheri, Abuzar
    Abbasi, Alireza
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2010, 47 (03) : 611 - 615
  • [50] A facile and regioselective synthesis of rimonabant through an enamine-directed 1,3-dipolar cycloaddition
    Donohue, Sean R.
    Halldin, Christer
    Pike, Victor W.
    TETRAHEDRON LETTERS, 2008, 49 (17) : 2789 - 2791