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Methodologies for the synthesis of bioactive terpenes

Abstract

The synthesis of bioactive sesqui- and diterpenoids is of continuing relevance. We present two distinct methodologies for the synthesis of polycyclic systems associated with such natural products. The Diels-Alder reaction of para-benzoquinones and their nitrogen derivatives, with simple dienes, leads to bi- and tricyclic products with structures which are ready for transformation into various groups of terpenoids, with predictable chemo-, regio- and stereoselectivity. On the other hand, the ring expansion of (R)-(-)-carvone into a chiral enantiopure cycloheptenone, followed by alkylations and ring closing metathesis, leads to the perhydroazulene system found in several sesqui- and diterpenoids. The experimental work is being linked to computer calculations, from simple conformational analysis of intermediates, to the determination of activation energies of the reactions. (AU)

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Scientific publications (23)
(References retrieved automatically from Web of Science and SciELO through information on FAPESP grants and their corresponding numbers as mentioned in the publications by the authors)
DE SOUZA, JULIANA M.; BROCKSOM, TIMOTHY J.; MCQUADE, D. TYLER; DE OLIVEIRA, KLEBER T. Continuous Endoperoxidation of Conjugated Dienes and Subsequent Rearrangements Leading to C-H Oxidized Synthons. Journal of Organic Chemistry, v. 83, n. 15, p. 7574-7585, AUG 3 2018. Web of Science Citations: 5.
BARTOLOMEU, ALOISIO DE A.; BROCKSOM, TIMOTHY J.; DA SILVA FILHO, LUIZ C.; DE OLIVEIRA, KLEBER T. Multicomponent reactions mediated by NbCl5 for the synthesis of phthalonitrile-quinoline dyads: Methodology, scope, mechanistic insights and applications in phthalocyanine synthesis. DYES AND PIGMENTS, v. 151, p. 391-402, APR 2018. Web of Science Citations: 1.
DE SOUZA, JULIANA M.; GALAVERNA, RENAN; DE SOUZA, ALINE A. N.; BROCKSOM, TIMOTHY J.; PASTRE, JULIO C.; DE SOUZA, RODRIGO O. M. A.; DE OLIVEIRA, KLEBER T. Impact of continuous flow chemistry in the synthesis of natural products and active pharmaceutical ingredients. Anais da Academia Brasileira de Ciências, v. 90, n. 2, p. 1131-1174, 2018. Web of Science Citations: 8.
JULIANA M. DE SOUZA; RENAN GALAVERNA; ALINE A.N. DE SOUZA; TIMOTHY J. BROCKSOM; JULIO C. PASTRE; RODRIGO O.M.A. DE SOUZA; KLEBER T. DE OLIVEIRA. Impact of continuous flow chemistry in the synthesis of natural products and active pharmaceutical ingredients. Anais da Academia Brasileira de Ciências, v. 90, n. 1, p. -, 2018.
CARMONA-VARGAS, CHRISTIAN C.; ALVES, LEANDRO DE C.; BROCKSOM, TIMOTHY J.; DE OLIVEIRA, KLEBER T. Combining batch and continuous flow setups in the end-to-end synthesis of naturally occurring curcuminoids. REACTION CHEMISTRY & ENGINEERING, v. 2, n. 3, p. 366-374, JUN 2017. Web of Science Citations: 9.
TIMOTHY J. BROCKSOM; KLEBER T. DE OLIVEIRA; ANDRÉ L. DESIDERÁ. The Chemistry of the Sesquiterpene Alkaloids. Journal of the Brazilian Chemical Society, v. 28, n. 6, p. 933-942, Jun. 2017. Web of Science Citations: 4.
GOBO, NICHOLAS R. S.; BROCKSOM, TIMOTHY J.; DE OLIVEIRA, KLEBER T. Soluble and Non-Aggregated Phthalocyanines: Synthesis, Mechanistic Aspects and Their Main Building Blocks. CURRENT ORGANIC SYNTHESIS, v. 14, n. 8, p. 1132-1155, 2017. Web of Science Citations: 1.
DIN, ZIA UD; FILL, TAICIA P.; CAROLINA DONATONI, M.; DOS SANTOS, CAROLINA A. A.; BROCKSOM, TIMOTHY J.; RODRIGUES-FILHO, E. Microbial diversification of Diels-Alder cycloadducts by whole cells of Penicillium brasilianum. MOLECULAR DIVERSITY, v. 20, n. 4, p. 877-885, NOV 2016. Web of Science Citations: 3.
DONATONI, MARIA C.; VIEIRA, YGOR W.; BROCKSOM, TIMOTHY J.; RABELO, ADRIANO C.; LEITE, EDSON R.; DE OLIVEIRA, KLEBER T. One-pot sequential functionalizations of meso-tetrathienylporphyrins via Heck-Mizoroki cross-coupling reactions. Tetrahedron Letters, v. 57, n. 27-28, p. 3016-3020, JUL 6 2016. Web of Science Citations: 4.
BARONA-CASTANO, JUAN C.; CARMONA-VARGAS, CHRISTIAN C.; BROCKSOM, TIMOTHY J.; DE OLIVEIRA, KLEBER T. Porphyrins as Catalysts in Scalable Organic Reactions. Molecules, v. 21, n. 3 MAR 2016. Web of Science Citations: 56.
DE ASSIS, FRANCISCO F.; FERREIRA, MARCO A. B.; BROCKSOM, TIMOTHY J.; DE OLIVEIRA, KLEBER T. NIR bacteriochlorin chromophores accessed by Heck and Sonogashira cross-coupling reactions on a tetrabromobacteriochlorin derivative. ORGANIC & BIOMOLECULAR CHEMISTRY, v. 14, n. 4, p. 1402-1412, 2016. Web of Science Citations: 8.
MOMO, PATRICIA B.; SAMPAIO, OLIVIA M.; BROCKSOM, TIMOTHY J.; DE OLIVEIRA, KLEBER T. Selective Vilsmeier-Haack aryl-formylations of tetrathienylporphyrin and its Ni(II) complex. Journal of Porphyrins and Phthalocyanines, v. 19, n. 6, p. 745-752, JUN 2015. Web of Science Citations: 1.
ALVES, LEANDRO DE C.; DESIDERA, ANDRE L.; DE OLIVEIRA, KLEBER T.; NEWTON, SEAN; LEY, STEVEN V.; BROCKSOM, TIMOTHY J. A practical deca-gram scale ring expansion of (R)-(-)-carvone to (R)-(+)-3-methyl-6-isopropenyl-cyclohept-3-enone-1. ORGANIC & BIOMOLECULAR CHEMISTRY, v. 13, n. 28, p. 7633-7642, 2015. Web of Science Citations: 7.
BROCKSOM, TIMOTHY JOHN; DESIDERA, ANDRE LUIZ; ALVES, LEANDRO DE CARVALHO; DE OLIVEIRA, KLEBER THIAGO. The New Directions of Organic Synthesis. CURRENT ORGANIC SYNTHESIS, v. 12, n. 5, p. 496-522, 2015. Web of Science Citations: 6.
MOMO, PATRICIA B.; BELLETE, BARBARA S.; BROCKSOM, TIMOTHY J.; DE SOUZA, RODRIGO O. M. A.; DE OLIVEIRA, KLEBER T. Exploiting novel process windows for the synthesis of meso-substituted porphyrins under continuous flow conditions. RSC ADVANCES, v. 5, n. 102, p. 84350-84355, 2015. Web of Science Citations: 11.
ULIANA, MARCIANA P.; SERVILHA, BRUNO M.; ALEXOPOULOS, OLGA; DE OLIVEIRA, KLEBER T.; TORMENA, CLAUDIO F.; FERREIRA, MARCO A. B.; BROCKSOM, TIMOTHY J. The Diels-Alder reactions of para-benzoquinone nitrogen-derivatives: an experimental and theoretical study. Tetrahedron, v. 70, n. 39, p. 6963-6973, SEP 30 2014. Web of Science Citations: 4.
MOMO, PATRICIA BETONI; PAVANI, CHRISTIANE; BAPTISTA, MAURICIO S.; BROCKSOM, TIMOTHY JOHN; DE OLIVEIRA, KLEBER THIAGO. Chemical Transformations and Photophysical Properties of meso-Tetrathienyl-Substituted Porphyrin Derivatives. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, n. 21, p. 4536-4547, JUL 2014. Web of Science Citations: 11.
BARBOSA, LAYLA R.; VIEIRA, YGOR W.; LACERDA, JR., VALDEMAR; DE OLIVEIRA, KLEBER T.; DOS SANTOS, REGINALDO B.; GRECO, SANDRO J.; NETO, ALVARO C.; DE CASTRO, EUSTAQUIO V. R.; BROCKSOM, TIMOTHY J. Unequivocal structural assignments of three cycloheptenoid intermediates for guaiane sesquiterpenes: an experimental and theoretical approach. Magnetic Resonance in Chemistry, v. 52, n. 6, p. 318-328, JUN 2014. Web of Science Citations: 2.
DONATONI, MARIA C.; JUNIOR, GILMAR A. B.; DE OLIVEIRA, KLEBER T.; ANDO, ROMULO A.; BROCKSOM, TIMOTHY J.; DOS SANTOS, ALCINDO A. Solvent-free Diels-Alder reactions catalyzed by FeCl3 on Aerosil((R)) silica. Tetrahedron, v. 70, n. 20, p. 3231-3238, MAY 20 2014. Web of Science Citations: 8.
DE SOUZA, JULIANA M.; DE ASSIS, FRANCISCO F.; CARVALHO, CARLA M. B.; CAVALEIRO, JOSE A. S.; BROCKSOM, TIMOTHY J.; DE OLIVEIRA, KLEBER T. Synthesis of non-aggregating chlorins and isobacteriochlorins from meso-tetralcis(pentafluorophenyl)porphyrin: a study using 1,3-dipolar cycloadditions under mild conditions. Tetrahedron Letters, v. 55, n. 8, p. 1491-1495, FEB 19 2014. Web of Science Citations: 14.
DE OLIVEIRA, KLEBER T.; MOMO, PATRICIA B.; DE ASSIS, FRANCISCO F.; FERREIRA, MARCO A. B.; BROCKSOM, TIMOTHY J. Chlorins: Natural Sources, Synthetic Developments and Main Applications. CURRENT ORGANIC SYNTHESIS, v. 11, n. 1, p. 42-58, FEB 2014. Web of Science Citations: 31.
ULIANA, MARCIANA P.; PIRES, LAYLA; PRATAVIEIRA, SEBASTIAO; BROCKSOM, TIMOTHY J.; DE OLIVEIRA, KLEBER T.; BAGNATO, VANDERLEI S.; KURACHI, CRISTINA. Photobiological characteristics of chlorophyll a derivatives as microbial PDT agents. PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, v. 13, n. 8, p. 1137-1145, 2014. Web of Science Citations: 19.
BRITO CARVALHO, CARLA MARISA; FUJITA, MARTA AKEMI; BROCKSOM, TIMOTHY JOHN; DE OLIVEIRA, KLEBER THIAGO. Synthesis and photophysical evaluations of beta-fused uracil-porphyrin derivatives. Tetrahedron, v. 69, n. 47, p. 9986-9993, NOV 25 2013. Web of Science Citations: 6.

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