An Integrated Flow and Batch-Based Approach for the Synthesis of O-Methyl Siphonazole

被引:34
作者
Baumann, Marcus [1 ]
Baxendale, Ian R. [1 ]
Brasholz, Malte [1 ]
Hayward, John J. [1 ]
Ley, Steven V. [1 ]
Nikbin, Nikzad [1 ]
机构
[1] Univ Cambridge, Dept Chem, Innovat Technol Ctr, Cambridge CB2 1EW, England
基金
英国工程与自然科学研究理事会;
关键词
oxazoles; Claisen condensation; flow chemistry; microreactors; solid-supported reagents; MULTISTEP SYNTHESIS; BENGAZOLE-A; CHEMISTRY; REACTOR; POTENT; EFFICIENT; REAGENTS; OPTIMIZATION; TECHNOLOGY; CONVERSION;
D O I
10.1055/s-0030-1260573
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The bisoxazole containing natural product O-methyl siphonazole was assembled using a suite of microreactors via a flow-based approach in concert with traditional batch methods. The use of a toolbox of solid-supported scavengers and reagents to aid purification afforded the natural product in a total of nine steps.
引用
收藏
页码:1375 / 1380
页数:6
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共 79 条
  • [1] Chemoselective reaction system using a two inlet micro-flow reactor: application to carbonyl allylation
    Amemiya, Fumihiro
    Fuse, Keishi
    Fuchigami, Toshio
    Atobe, Mahito
    [J]. CHEMICAL COMMUNICATIONS, 2010, 46 (16) : 2730 - 2732
  • [2] Continuous flow processing from microreactors to mesoscale: the Bohlmann-Rahtz cyclodehydration reaction
    Bagley, Mark C.
    Fusillo, Vincenzo
    Jenkins, Robert L.
    Lubinu, M. Caterina
    Mason, Christopher
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (09) : 2245 - 2251
  • [3] Synthesis of functionalised oxazoles and bis-oxazoles
    Bagley, MC
    Buck, RT
    Hind, SL
    Moody, CJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (03): : 591 - 600
  • [4] Synthesis of β-Keto Esters In-Flow and Rapid Access to Substituted Pyrimidines
    Bartrum, Hannah E.
    Blakemore, David C.
    Moody, Christopher J.
    Hayes, Christopher J.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (24) : 8674 - 8676
  • [5] The use of diethylaminosulfur trifluoride (DAST) for fluorination in a continuous-flow microreactor
    Baumann, Marcus
    Baxendale, Ian R.
    Ley, Steven V.
    [J]. SYNLETT, 2008, (14) : 2111 - 2114
  • [6] A modular flow reactor for performing Curtius rearrangements as a continuous flow process
    Baumann, Marcus
    Baxendale, Ian R.
    Ley, Steven V.
    Nikbin, Nikzad
    Smith, Christopher D.
    Tierney, Jason P.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (09) : 1577 - 1586
  • [7] Fully automated continuous flow synthesis of 4,5-disubstituted oxazoles
    Baumann, Marcus
    Baxendale, Ian R.
    Ley, Steven V.
    Smith, Christoper D.
    Tranmer, Geoffrey K.
    [J]. ORGANIC LETTERS, 2006, 8 (23) : 5231 - 5234
  • [8] SYNTHESIS OF HIGHLY SUBSTITUTED NITROPYRROLIDINES, NITROPYRROLIZINES AND NITROPYRROLES VIA MULTICOMPONENT-MULTISTEP SEQUENCES WITHIN A FLOW REACTOR
    Baumann, Marcus
    Baxendale, Ian R.
    Kirschning, Andreas
    Ley, Steven V.
    Wegner, Jens
    [J]. HETEROCYCLES, 2011, 82 (02) : 1297 - +
  • [9] The flow synthesis of heterocycles for natural product and medicinal chemistry applications
    Baumann, Marcus
    Baxendale, Ian R.
    Ley, Steven V.
    [J]. MOLECULAR DIVERSITY, 2011, 15 (03) : 613 - 630
  • [10] Development of fluorination methods using continuous-flow microreactors
    Baumann, Marcus
    Baxendale, Ian R.
    Martin, Laetitia J.
    Ley, Steven V.
    [J]. TETRAHEDRON, 2009, 65 (33) : 6611 - 6625