Organocatalytic enantioselective formal synthesis of HRV 3C-protease inhibitor (1R,3S)-thysanone

被引：32
|
作者：
Sawant, Rajiv T. [1 ]
Waghmode, Suresh B. [1 ]
机构：
[1] Univ Pune, Dept Chem, Pune 411007, Maharashtra, India
来源：
TETRAHEDRON | 2009年 / 65卷 / 08期
关键词：
Asymmetric alpha-aminooxylation; Praline; Pyranonaphthoquinones; Thysanone; Oxa-Pictet-Spengler cyclization; ASYMMETRIC ALPHA-AMINOXYLATION; DEOXY ANALOGS; THYSANONE; STEREOCHEMISTRY; AMINOOXYLATION; ALDEHYDES; 1,2-DIOLS;
D O I：
10.1016/j.tet.2008.12.060
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A short and efficient organocatalytic enantioselective formal synthesis of HRV 3C-protease inhibitor (1R,3S)-thysanone is achieved in a nine-step with 98.7% enantiomeric excess, by employing L-proline-catalyzed asymmetric of alpha-aminooxylation of aldehyde and Oxa-Pictet-Spengler cyclization as the key steps. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1599 / 1602
页数：4
相关论文
共 41 条
  • [1] Enantioselective Synthesis of the 3C-Protease Inhibitor (-)-Thysanone by a Staunton-Weinreb Annulation Strategy
    Sperry, Jonathan
    Yuen, Tsz Ying
    Brimble, Margaret A.
    SYNTHESIS-STUTTGART, 2009, (15): : 2561 - 2569
  • [2] Formal Synthesis of the Human Rhinovirus 3C Protease Inhibitor (-)-Thysanone
    Mulay, Sandip V.
    Gholap, Sachin P.
    Fernandes, Rodney A.
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 4 (06) : 560 - 566
  • [3] Stereoselective synthesis of deoxy analogues of the 3C-protease inhibitor thysanone
    Brimble, MA
    Elliott, RJR
    TETRAHEDRON, 2002, 58 (01) : 183 - 189
  • [4] Synthesis and evaluation of 9-deoxy analogues of (-)-thysanone, an inhibitor of HRV 3C protease
    Jeong, Joo Young
    Sperry, Jonathan
    Taylor, John A.
    Brimble, Margaret A.
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 87 : 220 - 227
  • [5] An efficient enantioselective synthesis of the 3C protease inhibitor (-)-thysanone
    Sperry, Jonathan
    Brimble, Margaret A.
    SYNLETT, 2008, (12) : 1910 - 1912
  • [6] Chemoenzymatic synthesis of deoxy analogues of the DNA topoisomerase II inhibitor eleutherin and the 3C-protease inhibitor thysanone
    Bachu, Prabhakar
    Sperry, Jonathan
    Brimble, Margaret A.
    TETRAHEDRON, 2008, 64 (21) : 4827 - 4834
  • [7] Iridium-Catalysed C-H Borylation Facilitates a Total Synthesis of the HRV 3C Protease Inhibitor (±)-Thysanone
    Schuenemann, Katrin
    Furkert, Daniel P.
    Connelly, Stephen
    Fraser, John D.
    Sperry, Jonathan
    Brimble, Margaret A.
    SYNLETT, 2014, 25 (04) : 556 - 558
  • [8] Synthesis of the 2-methylene analogue of the HRV 3C protease inhibitor thysanone (2-carbathysanone)
    Schuenemann, Katrin
    Furkert, Daniel P.
    Choi, Eun Cho
    Connelly, Stephen
    Fraser, John D.
    Sperry, Jonathan
    Brimble, Margaret A.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (06) : 905 - 912
  • [9] STRUCTURE AND STEREOCHEMISTRY OF THYSANONE - A NOVEL HUMAN RHINOVIRUS 3C-PROTEASE INHIBITOR FROM THYSANOPHORA-PENICILLOIDES
    SINGH, SB
    CORDINGLEY, MG
    BALL, RG
    SMITH, JL
    DOMBROWSKI, AW
    GOETZ, MA
    TETRAHEDRON LETTERS, 1991, 32 (39) : 5279 - 5282
  • [10] Synthesis and Biological Evaluation of 7-Deoxy Analogues of the Human Rhinovirus 3C Protease Inhibitor Thysanone
    Schuenemann, Katrin
    Furkert, Daniel P.
    Connelly, Stephen
    Fraser, John D.
    Sperry, Jonathan
    Brimble, Margaret A.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (01) : 122 - 128
12345