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Synthesis 2015; 47(23): 3711-3716
DOI: 10.1055/s-0035-1560070
DOI: 10.1055/s-0035-1560070
paper
A First Synthesis of Bis(benzoxazole) Natural Products: Nataxazole and AJI9561 via Benzoxazole C–H Activation
Further Information
Publication History
Received: 25 May 2015
Accepted after revision: 07 July 2015
Publication Date:
18 August 2015 (online)
Abstract
Concise and efficient syntheses of nataxazole and AJI9561 have been accomplished. We also demonstrate a convenient route to obtain the related natural product UK-1. The key step involves C–H activation of a benzoxazole in the presence of ortho-iodoanilides using a copper(I) iodide/Xantphos/palladium(II) acetate system.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560070.
- Supporting Information
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References
- 1 Berdy J. J. Antibiot. 2005; 58: 1
- 2a Ueki M, Ueno K, Miyadoh S, Abe K, Shibata K, Taniguchi M, Oi S. J. Antibiot. 1993; 46: 1089
- 2b Shibata K, Kashiwada M, Ueki M, Taniguchi M. J. Antibiot. 1993; 46: 1095
- 3a Ward DN, Talley DC, Tavag M, Menji S, Schaughency P, Baier A, Smith PJ. Bioorg. Med. Chem. Lett. 2014; 24: 609
- 3b Huang S.-T, Hsei I.-J, Chen C. Bioorg. Med. Chem. 2006; 14: 6106
- 3c Wang BN, Maghami N, Goodlin VL, Smith PJ. Bioorg. Med. Chem. Lett. 2004; 14: 3221
- 3d Ueki M, Taniguchi M. J. Antibiot. 1997; 50: 788
- 3e Kumar D, Jacob MR, Reynold MB, Kerwin SM. Bioorg. Med. Chem. 2002; 10: 3997
- 3f Kerwin SM. US 2005/0004188 A1, 2005
- 4a McKee ML, Kerwin SM. Bioorg. Med. Chem. 2008; 16: 1775
- 4b Reyzar ML, Broadbelt JS, Kerwin SM, Kumar D. Nucleic Acids Res. 2001; 29: e103
- 4c Reynold MB, Deluka MR, Kerwin SM. Bioorg. Chem. 1999; 27: 326
- 5 Sato S, Kajiura T, Noguchi M, Takehana K, Kobayashi T, Tsuji T. J. Antibiot. 2001; 54: 102
- 6 Sommer PS. M, Almeida RC, Schneider K, Beil W, Süssmuth RD, Fiedler H.-P. J. Antibiot. 2008; 61: 683
- 7 Cano-Prieto C, García-Salcedo R, Sánchez-Hidalgo M, Braña AF, Fiedler H.-P, Méndez C, Salas JA, Olano C. ChemBioChem 2015; 16: 1461
- 8 DeLuca MR, Kerwin SM. Tetrahedron Lett. 1997; 38: 199
- 9a Alberico D, Scott ME, Lautens M. Chem. Rev. 2007; 107: 174
- 9b Seregin IV, Gevorgyan V. Chem. Soc. Rev. 2007; 36: 1173
- 9c Verrier C, Lassalas P, Théveau L, Quéguiner G, Trécourt F, Marsais F, Hoarau C. Beilstein J. Org. Chem. 2011; 7: 1584
- 9d Chen X, Engle KM, Wang D, Yu JQ. Angew. Chem. 2009; 121: 5196
- 9e Kakiuchi F, Chatani N. Adv. Synth. Catal. 2003; 345: 1077
- 9f Ackermann L, Vicente R, Kapdi AR. Angew. Chem. Int. Ed. 2009; 48: 9792
-
9g Ritleng V, Sirlin C, Pfeffer M. Chem. Rev. 2002; 102: 1731
- 9h Yan XM, Mao XR, Huang ZZ. Heterocycles 2011; 83: 1371
- 9i Huang J, Chan J, Chen Y, Borths CJ, Baucom KD, Larsen RD, Faul MM. J. Am. Chem. Soc. 2010; 132: 3674
- 10 Sasmal S, Sen I, Hall RG, Pal S. Tetrahedron Lett. 2015; 56: 1374
- 11 Rewcastle GW, Atwell GJ, Baguley BC, Calveley SB, Denny WA. J. Med. Chem. 1989; 32: 793
- 12 Goldstein SW, Dambeck PJ. J. Heterocycl. Chem. 1990; 27: 335
- 13 Tipparaju SK, Joyasawal S, Pieroni M, Kaiser M, Brun R, Kozikowski AP. J. Med. Chem. 2008; 51: 7344