Guía de estudio de gira de campo a la reserva natural el Arenal

[1] W. Eberbach, In Houben-Weyl Methoden der Organischem Chemie, (5th Ed.), Vol. E6a, Thieme: Stuttgart, 1994, 16.

[2] Y. Kobayashi, M. Nakano, C. Biju Kumer, K. Kishihara. “Efficient Conditions for Conversion of 2-Substituted Furans into 4-Oxygenated 2-Enoic Acids and Its Application to Synthesis of (+)- Aspicilin, (+)-Patulolide A, and (-)-Pyrenophorin”, Journal of Organic Chemistry, 1998, 63, 7505-7515.

[3] T. H. Brown, M. A. Armitage, R. C. Blackmore, P. Blurton, G. J. Durant, C. R. Ganellin, R. G. Ife, M. E. Parsons, D. A. Rawlings, B. P. Slingsby, European Journal of Medicinal Chemistry,

1990, 25, 217-226.

[4] D. K. Barma, A. Kundu, R. Baati, C. Mioskowski, J. R. Falck, “A Convenient Preparation of 3- Substituted Furans: Synthesis of Perillene and Dendrolasin”, Organic Letters, 2002, 4, 1387- 1389.

[5] S. Ma, L. Li. “Palladium-Catalyzed Cyclization Reaction of Allylic Bromides with 1,2-Dienyl Ketones. An Efficient Synthesis of 3-Allylic Polysubstituted Furans”, Organic Letters, 2000, 2, 941-944; C-C. Pai, R-S. Liu, “Enantiocontrolled Construction of Tricyclic Furan Derivatives via an Asymmetric Diels-Alder Reaction”, Organic Letters, 2001, 3, 1295-1298; F. Stauffer, R. Neier, “Synthesis of Tri- and Tetrasubstituted Furans Catalyzed by Trifluoroacetic Acid”, Orgamic Letters, 2000, 2, 3535-3537.

[6] J. McMurry. “Organic Chemistry”, (4th Ed.), Brooks and Cole publishing, U.S.A., 1996, 500- 501, 762. ISBN 0-534-23832-7.

[7] J. March. “Advanced Organic Chemistry: Reactions, Mechanisms and Structure”, (4th _{Ed.), John}

Wiley and Sons, N.Y., 1992, 30, 45, 228, 1091-1093, 795-796, 741-742. ISBN 0-471-58148-8. [8] B. S. Furniss, A. J. Hannaford, P. W. G. Smith, A. R. Tatchell. “Vogel’s Textbook of Practical

Organic Chemistry”, (5th _{Ed.), Longman Group, U.K. Ltd., 1989, 1146-1148. ISBN 0-582-}

46236-3.

[9] J. D. Roberts, M. C. Caserio. “Basic Principles of Organic Chemistry”, W. A. Benjamin Inc., New-York, 1964, 998.

[10] N. Bodor, M. J. S. Dewar, A. J. Harget. “Ground States of Conjugated Molecules. XIX. Tautomerism of Heteraromatic Hydroxy and Amino Derivatives and Nucleotide Bases”, Journal of the American Chemical Society, 1970, 92, 2929-2936.

[11] I. G. John, L. Radom. “Conformations, Stabilities, and Charge Distributions in 2- and 3- Monosubstituted Furans. An ab initio Molecular Orbital Study”, Journal of the American Chemical Society, 1978, 100, 3981-3991.

[12] M. A. Shokhen, V. G. Andrianov, A. V. Eremeev, S. V. Barmina. “Dependence of the reactivity of five membered aromatic heterocycles on their structure. 2: Effect of aza substitution on the proton affinity of aminofurans”, Khimiya Geterotsiklicheskikh Soedinenii, 1987, 2, 175-178. [13] R. Kuhn, G. Krüger. “Das Chromogen III Der Morgan-Elson-Reaktion”, Chemie Berichte, 1957,

90, 264-277.

[14] R. R. Burtner. “Orientation in the Furan Nucleus. VIII. -Acylaminofurans”, Journal of the American Chemical Society, 1934, 56, 666-667; H. M. Singleton, W. R. Edwards. “Preparation and Properties of Some Derivatives of 2-Aminofuran”. Journal of the American Chemical Society, 1938, 60, 540-544.

[15] J. D. Prugh, W. C. McCarthy. “Heterocyclic Amines III. 3-Dimethylaminofuran”, Journal of Medicinal Chemistry, 1966, 9, 254-255.

[16] R. Kuhn, G. Krüger. “3-Acetamino-furan aus N-Acetyl-D-glucosamin; ein Beirag zur Theorie der Morgan-Elson-Reaktion”, Chemie Berichte, 1956, 6, 1473-1486 and references therein; S. F. Mason. “The Tautomerization of N-Heterocyclic Hydroxy-Compounds. Part II. Ultraviolet spectra”, Journal of the Chemical Society, 1957, 5010-5017.

[17] T. Shioiri, K. Ninomiya, S. Yamada. “Diphenylphosphoryl azide. New convenient reagent for a modified Curtius reaction and for peptide synthesis”, Journal of the American Chemical Society,

1972, 94, 6203-6205.

[18] M. M. Campbell, A. D. Kaye, M. Sainsbury, “3-Acylamino Furan”, Tetrahedron, 1982, 38, 2783-2786.

[19] D. T. Davies. “Aromatic Heterocyclic Chemistry”, Oxford University Press, N.Y., 1997, 14-17. ISBN: 0-19-855660-8.

[20] B. T. Freure, J. R. Johnson. “The Structure of Nitrofuran and the Mechanism of Nitration in the Furan Series”, Journal of the American Chemical Society, 1931, 53, 1142-1147.

[21] A. Padwa, M. Dimitroff, A. G. Waterson, T. Wu. “Diels-Alder Reaction of 2-Amino-Substituted Furans as a Method for Preparing Substituted Anilines”, Journal of Organic Chemistry, 1997, 62, 4088-4096.

[22] J. M. Tedder, A. Nechvatal, A. W. Murray, J. Carnduff. “Basic Organic Chemistry: Part 3”, John Wiley and Sons Ltd., London, 1970, 96-97. ISBN: 0-471-85013-6.

[23] L. C. Raiford, W. G. Huey, “Reduction of the 2-nitrophenyl esters of certain acids”, Journal of Organic Chemistry, 1941, 6, 858-866.

[24] Y. L. Gol’dfarb, Y. B. Vol’kenshtein, B. V. Lopatin. “Bromination and Chloromethylation of Thiophen-2-aldehyde In the Presence of an Excess of Aluminium Chloride”, Zhurnal Obshchei Khimii, 1964, 34, 969-977.

[25] D. J. Chadwick, J. Chambers, D. Meakins, R. L. Snowden. “Esters of Furan-, Thiophen- and N- Methylpyrrole-2-carboxylic Acids, Bromination of Methyl Furan-2-carboxylate, Furan-2- carbaldehyde, and Thiophen-2-carbaldehyde in the Presence of Aluminium Chloride”, Journal Chemical Society Perkin Transactions I, 1973, 1766-1773.

[26] R. Antonioletti, M. D’Auria, A. De Mico, G. Piancatelli, A. Scettri. “Photochemical Synthesis of 3- and 5-Aryl-2-furyl Derivatives”, Journal of the Chemical Society, Perkins Transactions I,

1985, 1285-1288.

[27] A. F. Shepard, N. R. Winslow, J. R. Johnson. “The Simple Halogen Derivatives of Furan”, Journal of the American Chemical Society, 1930, 52, 2083-2090.

[28] A. Togni, H. Grützmacher. “Catalytic Heterofunctionalization”, Wiley-VCH Verlag., 2001, ISBN: 3-527-30234-4.

[29] H. Tomori, J. M. Fox, S. L. Buchwald. “An Improved Synthesis of Functionalized Biphenyl- Based Phosphine Ligands”, Journal of Organic Chemistry, 2000, 65, 5334-5341.

[30] J. P. Wolfe, H. Tomori, J. P. Sadighi, J. Yin, S. L. Buchwald. “Simple, Efficient Catalyst System for the Palladium-Catalyzed Amination of Aryl Chlorides, Bromides and Triflates”, Journal of Organic Chemistry, 2000, 65, 1158-1174.

[31] M. C. Harris, S. L. Buchwald. “One-Pot Synthesis of Unsymmetrical Triarylamines from Aniline Precursors”, Journal of Organic Chemistry, 2000, 65, 5327-5333.

[32] R. Antonioletti, M. D’Auria, A. De Mico, G. Piancatelli, A. Scettri. “Photochemical Synthesis of 3- and 5-Aryl-2-furyl Derivatives”, Journal of the Chemical Society, Perkins Transactions I,

1985, 1285-1288. **find paper specifically for 5-bromofuraldehyde.

[33] Y. L. Gol’dfarb, L. D. Tarasova. “Synthesis of 2,4-Disubstituted Furans”, Doklady Akademii Nauk SSSR, 1965, 163, 1393-1396.

[34] D. Todd. “The Wolff-Kishner Reduction, Organic Reactions, 1948, 4, 378-422; Huang-Minlon. “A Simple Modification of the Wolff-Kishner Reduction”, Journal of the American Chemical Society, 1946, 68, 2487-2488.

[35] B. Majoie. “2,3-Dibromofuran by Bromination of Furancarboxaldehydes”, Societe de Recherches Industrielles (“SORI”), Patent U.S. 3,714,197, (1971), CAN: 74:76318, AN: 1971:76318.

[36] Katsumura, S., Ichikawa, K., Mori, H. “Synthesis of Tetrasubstituted Butenolide, Bromobeckerelide by Regioselective Lithiation of Furan Followed by Photosensitized Oxygenation of -Silylfuran”, Chemistry Letters, 1993, 9, 1525-1528.

[37] T. Cohen, R. A. Schambach. “Copper-quinoline decarboxylation”, Journal of the American Chemical Society, 1970, 92, 3189-3190.

[38] H. Gilman, G. F. Wright. “Furan Mercurials”. Journal of the American Chemical Society, 1933, 55, 3302-3313.

[39] J. P. Wolfe, S. L. Buchwald. “Scope and Limitations of the Pd/BINAP catalyzed amination of aryl bromides”. Journal of Organic Chemistry, 2000, 65, 1144-1157.

[40] F. E. Goodson, S. I. Hauck, J. F. Hartwig. “Palladium-Catalyzed Synthesis of Pure, Regiodefined Polymeric Triarylamines”. Journal of the American Chemical Society, 1999, 121, 7527-7539 and references therein.

[41] V. Farina. “Comprehensive Organometallic Chemistry”, (2nd _{Ed.), Pergamon Press, Oxford,} 1995, Vol. 12, 160-240.

[42] A. M. Redman, J. Dumas, W. J. Scott. “Preparation of 5-Substituted 3-Aminofuran-2- Carboxylate Esters”, Organic Letters, 2000, 2, 2061-2063.

[43] C. Ma, H. Ding, G. Wu, Y. Yang. “Facile Synthesis of Highly Substituted 3-Aminofurans from thiazolium Salts, Aldehydes and Dimethyl Acetylene Dicarboxylate”, Journal of Organic Chemistry, 2005, 70, 8919-8923.

[44] S. Mageswaran, W. D. Ollis, D. A. Southam, I. O. Sutherland, Y. J. Thebtaranonth. “Base Catalysed Rearrangements Involving Ylide Intermediates. Part 11. Rearrangements of 3- Phenylprop-2-ylnylammonium Ylides”, Journal of the Chemical Society Perkin Transactions 1,

1981, 1969-1980.

[45] J. Ficini, M. Claeys, J. C. Depezau. “Sur une synthese inattendue d'amino-3 furannes”, Tetrahedron Letters, 1973, 14, 3353-3355.

[46] J.-N. Cui, T. Ema, T. Sakai, M. Utaka. “Control of Enantioselectivity in the Bakers Yeast Asymmetric Reduction of -Chloro- -diketones to -Chloro-(S)- -hydroxy ketones”, Tetrahedron: Asymmetry, 1998, 9, 2681-2692.

[47] J.K. Seydel, E.R. Garrett, W. Diller, K.J. Schaper. “5-Methyl-3(2H)furanone from Acid Catalyzed Solvolysis of 2-Deoxy-D-Ribose”, Journal of Pharmaceutical Sciences, 1967, 56, 858-862.

[48] A. Hofmann, W. v. Philipsborn, C. H. Eugster. NMR. “Untersuchungen an einfachen Furenidon system. Synthese des unsubstituierten 2_{-Furenidons-(4) ( -Hydroxyfuran)”, Helvetica Chimica}

Acta, 1965, 48, 1322-1331.

[49] B. P. Gusev, V. F. Kucherov. “Reaction of Diacetylenic Glycols with Amines”, Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1974, 1, 206-208.

[50] K. Bowden, E. A. Braude, E. R. H. Jones, B. C. L. Weedon. “Research on Acetylenic Compounds. Part II. (A) The Addition of Amines to Ethynyl Ketones. (B) Auxochromic

Properties and Conjugating Power of the Amino Group”, Journal of the Chemical Society, 1946, 45-52.

[51] I. M. Heilbron, E. R. H. Jones, P. Smith, B. C. L. Weedon. “Researches on Acetylenic Compounds. Part IV. The Hydration of Some Acetylentlcarbinols Derived from , -Unsaturated Aldehydes”, Journal of the Chemical Society, 1946, 54-58.

[52] E. Duranti, C. Balsamini. “Synthesis of 4-Oxo-2-alkyn-1-ols”, Synthesis, 1974, 357-358.

[53] H. B. Henbest, E. R. H. Jones, I. M. S. Walls. “Researches on Acetylenic Compounds. Part XXVI. Further Reformatsky Reactions with Propargyl Bromides”, Journal of the Chemical Society, 1950, 3646-3650.

[54] E. Pretsch, P. Bühlmann, C. Affolter. “Structure Determination of Organic Compounds: Tables of Spectral Data”, Springer-Verlag, New York, 2000, 358-360, 323-324. ISBN: 3-540-67815-8. [55] M. Journet, D. Cai, L. M. di Michele, R. D. Larsen. “Highly Efficient Synthesis of , -

Acetylenic Aldehydes From Terminal Alkynes Using DMF As the Formylating Reagent”, Tetrahedron Letters, 1998, 39, 6427-6428.

[56] J. P. Michael, C. B. de Koning, D. Gravestock, G. D. Hosken, A. S. Howard, C. M. Jungmann, R. W. M. Krause, A. S. Parsons, S. C. Pelly, T. V. Stanbury. “Enaminones: Versatile Intermediates for Natural Product Synthesis”, Pure and Applied Chemistry, 1999, 71, 979-988. [57] R. Bruckner. “Advanced Organic Chemistry: Reaction Mechanisms”. Hardcourt Press,

California, 2002, 415. ISBN: 0-12-138110-2.

[58] J. B. Lambert, E. P. Mazzola. Nuclear Magnetic Resonance Spectroscopy: An Introduction to Principles, Applications and Experimental Methods, Prentice Hall publishing, New Jersey, 2003, 115. ISBN 0130890669.

[59] R. H. Schlessinger, T. R. R. Pettus, J. P. Springer, K. Hoogsteen. “Diastereoselective Diels-Alder reactions Using Furan Substituted with a Nonracemic Amine”, Journal of Organic Chemistry,

1994, 59, 3246-3247.

[60] R. H. Schlessinger, C. P. Bergstrom. “Enantioselective Synthesis of (+)-Cyclophellitol”, Journal of Organic Chemistry, 1995, 60, 16-17.

[61] D. Enders, H. Eichenauer. “Assymetrische Synthesen via metallierte chirale Hydrazone. Enantioselective Alkylierung von cyclischen Ketonen und Aldehyden”, Chemie Berichte, 1979, 112, 2933-2960.

[62] R. B. Walker, D. S. Moore, M. D. Massey. “Mass Spectra of Some Oxazolidines Formed by Reaction of Ephedrine and Pseudoephedrine with Aliphatic Ketones”, Organic Mass Spectrometry, 1989, 24, 345-346.

[63] J. B. Hyne. “Nuclear Magnetic Resonance Spectra and Configuration. The N.M.R. Spectra of Diastereoisomeric Heterocyclic Derivatives of the Ephedrines”, Journal of the American Chemical Society, 1959, 81, 6058-6061.

[64] M. Johansen, H. Bundgaard. “Prodrugs as Delivery Systems. XXV: Hydrolysis of Oxazolidines - A Potential New Prodrug Type”, Journal of Pharmaceutical Sciences, 1983, 72, 1294-1298; S. A. Soliman. “Estimation of the Dissociation Constants of Some Unstable Diastereomeric Oxazolidines of Ephedrine and Pseudoephedrine”, Canadian Journal of Pharmaceutical Sciences. 1973, 8, 132-135.

Chapter 3