Coibacins A And B: Total Synthesis And Stereochemical Revision

dc.creatorCarneiro V.M.T.
dc.creatorAvila C.M.
dc.creatorBalunas M.J.
dc.creatorGerwick W.H.
dc.creatorPilli R.A.
dc.date2014
dc.date2015-06-25T17:54:28Z
dc.date2015-11-26T14:33:46Z
dc.date2015-06-25T17:54:28Z
dc.date2015-11-26T14:33:46Z
dc.date.accessioned2018-03-28T21:37:09Z
dc.date.available2018-03-28T21:37:09Z
dc.identifier
dc.identifierJournal Of Organic Chemistry. American Chemical Society, v. 79, n. 2, p. 630 - 642, 2014.
dc.identifier223263
dc.identifier10.1021/jo402339y
dc.identifierhttp://www.scopus.com/inward/record.url?eid=2-s2.0-84896768719&partnerID=40&md5=f18ed384f5a512f45760e6975dc995d9
dc.identifierhttp://www.repositorio.unicamp.br/handle/REPOSIP/86686
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/86686
dc.identifier2-s2.0-84896768719
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1247939
dc.descriptionThe interface between synthetic organic chemistry and natural products was explored in order to unravel the structure of coibacin A, a metabolite isolated from the marine cyanobacterium cf. Oscillatoria sp. that exhibits selective antileishmanial activity and potent antiinflammatory properties. Our synthetic plan focused on a convergent strategy that allows rapid access to the desired target by coupling of three key fragments involving E-selective Wittig and modified Julia olefinations. CD measurements and comparative HPLC analyses of the natural product and four synthetic stereoisomers led to determination of its absolute configuration, thus correcting the original assignment at C-5 and unambiguously establishing those at C-16 and C-18. Additionally, we synthesized coibacin B on the basis of the assignment of configuration for coibacin A. © 2013 American Chemical Society.
dc.description79
dc.description2
dc.description630
dc.description642
dc.descriptionGerwick, W.H., Moore, B.S., (2012) Chem. Biol., 19, p. 85
dc.descriptionLewy, D., Gauss, C.-M., Soenen, D., Boger, D., (2002) Curr. Med. Chem., 9, p. 2005
dc.descriptionStampwala, S.S., Bunge, R.H., Hurley, T.R., Willmer, N.E., Brankiewicz, A.J., Steinman, C.E., Smitka, T.A., French, J.C., (1983) J. Antibiot., 36, p. 1601
dc.descriptionTunac, J.B., Graham, B.D., Dobson, W.E., (1983) J. Antibiot., 36, p. 1595
dc.descriptionKalesse, M., Christmann, M., (2002) Synthesis, 981
dc.descriptionKobayashi, M., Higuchi, K., Murakami, N., Tajima, H., Aoki, S., (1997) Tetrahedron Lett., 38, p. 2859
dc.descriptionMurakami, N., Wang, W., Aoki, M., Tsutsui, Y., Higuchi, K., Aoki, S., Kobayashi, M., (1997) Tetrahedron Lett., 38, p. 5533
dc.descriptionMaier, M.E., (2009) Nat. Prod. Rep., 26, p. 1105
dc.descriptionNicolaou, K.C., Snyder, S.A., (2005) Angew. Chem. Int. Ed., 44, p. 1012
dc.descriptionBalunas, M.J., Grosso, M.F., Villa, F.A., Engene, N., McPhail, K.L., Tidgewell, K., Pineda, L.M., Gerwick, W.H., (2012) Org. Lett., 14, p. 3878
dc.descriptionGerwick, W.H., Proteau, P.J., Nagle, D.G., Hamel, E., Blokhin, A., Slate, D.L., (1994) J. Org. Chem., 59, p. 1243
dc.descriptionEdwards, D.J., Marquez, B.L., Nogle, L.M., McPhail, K., Goeger, D.E., Roberts, M.A., Gerwick, W.H., (2004) Chem. Biol., 11, p. 817
dc.descriptionGreen, L.C., Wagner, D.A., Glogowski, J., Skipper, P.L., Wishnok, J.S., Tannenbaum, S.R., (1982) Anal. Biochem., 126, p. 131
dc.descriptionBarcelos, R., Pastre, J., Caixeta, V., Vendramini-Costa, D., De Carvalho, J., Pilli, R., (2012) Bioorg. Med. Chem., 20, p. 3635
dc.descriptionBruder, M., Vendramini-Costa, D., De Carvalho, J., Pilli, R., (2013) Bioorg. Med. Chem., 21, p. 5107
dc.descriptionDe Fatima, A., Kohn, L.K., Antonio, M., De Carvalho, J., Pilli, R., (2005) Bioorg. Med. Chem., (13), p. 2927
dc.descriptionDe Fatima, A., Kohn, L.K., De Carvalho, J., Pilli, R., (2006) Bioorg. Med. Chem., (14), p. 622
dc.descriptionVendramini-Costa, D., De Castro, B.I.D., Ruiz, A., Marquissolo, C., Pilli, R., De Carvalho, J., (2010) Bioorg. Med. Chem., 18, p. 6742
dc.descriptionBoger, D.L., Ichikawa, S., Zhong, W., (2001) J. Am. Chem. Soc., 123, p. 4161
dc.descriptionCrimmins, M.T., King, B.W., (1998) J. Am. Chem. Soc., 120, p. 9084
dc.descriptionPhillips, D.J., Pillinger, K.S., Li, W., Taylor, A.E., Graham, A.E., (2006) Chem. Commun., 2280
dc.descriptionCharette, A.B., Juteau, H., (1994) J. Am. Chem. Soc., 116, p. 2651
dc.descriptionAlthough an axial orientation of the isopropyl substituent can be assumed on the basis of the anomeric effect, we have refrained from depicting the stereochemistry at C-1 because of a lack of unambiguous evidence, as the NOESY spectrum does show a weak correlation between H-1 and H5Correa Jr., I., Pilli, R., (2003) Angew. Chem., Int. Ed., (42), p. 3017
dc.descriptionCharette, A.B., Lebel, H., (1996) J. Am. Chem. Soc., 118, p. 10327
dc.descriptionChiralpak IA column (particle size 5 μm, dimensions 4.6 mm × 250 mm, 98% hexanes/2% i-PrOH, 1 mL/min). For chromatograms, see the Supporting InformationTamura, R., Saegusa, K., Kakihana, M., Oda, D., (1988) J. Org. Chem., 53, p. 2723
dc.descriptionAissa, C., (2009) Eur. J. Org. Chem., 1831
dc.descriptionLiu, P., Jacobsen, E.N., (2001) J. Am. Chem. Soc., 123, p. 10772
dc.descriptionSmith III, A.B., Brandt, B., (2001) Org. Lett., 3, p. 1685
dc.descriptionThe yield and diastereoisomeric ratio for the preparation of (5S,16S,18S)-25 were not optimized because they were obtained before the studies shown in Table 1Li, D., Zhao, Y., Ye, L., Chen, C., Zhang, J., (2010) Synthesis, p. 3325
dc.descriptionSunFire Prep C18 OBD column (particle size 5 μm, dimensions 19 mm × 100 mm, 60% MeCN/40% H2O, 17 mL/min)Chiralpak IA (particle Size 5 μm Dimensions 4.6 Mm × 250 Mm 90% MeCN10% MeOH 0.7 MLmin). For chromatograms, see the Supporting InformationBeecham, A., (1972) Tetrahedron, 28, p. 5543
dc.descriptionNagle, D.G., Geralds, R.S., Yoo, H.-D., Gerwick, W.H., Kim, T.-S., Nambu, M., White, J., (1995) Tetrahedron Lett., 36, p. 1189
dc.descriptionGu, L., Wang, B., Kulkarni, A., Geders, T.W., Grindberg, R.V., Gerwick, L., Hakansson, K., Sherman, D., (2009) Nature, 459, p. 731
dc.descriptionSunFire Prep C18 OBD column (particle size 5 μm, dimensions 19 mm × 100 mm, 55% MeCN/45% H2O, 17 mL/min)Guivisdalsky, P.N., Bittman, R., (1989) J. Org. Chem., 54, p. 4637
dc.descriptionHuckins, J.R., De Vicente, J., Rychnovsky, S.D., (2007) Org. Lett., 9, p. 4757
dc.descriptionStempel, G.H., Cross, R.P., Mariella, R.P., (1950) J. Am. Chem. Soc., 72, p. 2299
dc.descriptionKamal, A., Balakrishna, M., Reddy, P.V., Faazil, S., (2010) Tetrahedron: Asymmetry, 21, p. 2517
dc.descriptionHansen, T., (2002) Tetrahedron: Asymmetry, 13, p. 547
dc.descriptionFox, R.J., Lalic, G., Bergman, R.G., (2007) J. Am. Chem. Soc., 129, p. 14144
dc.descriptionKelly, B.D., Lambert, T.H., (2011) Org. Lett., 13, p. 740
dc.descriptionBahde, R.J., Rychnovsky, S.D., (2008) Org. Lett., 10, p. 4017
dc.languageen
dc.publisherAmerican Chemical Society
dc.relationJournal of Organic Chemistry
dc.rightsfechado
dc.sourceScopus
dc.titleCoibacins A And B: Total Synthesis And Stereochemical Revision
dc.typeArtículos de revistas


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