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Organocatalytic approach in the synthesis of natural & bioactiv e products

Pre študentov 1. ročníka biológie k predmetu Organická chémia

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Organocatalytic approach in the synthesis of natural & bioactiv e products

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  1. Pre študentov 1. ročníka biológie k predmetu Organická chémia Táto prezentácia odznela na seminári katedry organickej chémie Prif UK 15.10.2010. So súhlasom kolegu Mgr. Martina Huťku, PhD. dávam materiál k dispozícii študentom ako malú ukážku príspevku organických chemikov k poznaniu prírodných látok. Môže vam to poslúžiť aj ako inšpirácia výberu zlúčeniny na seminárnu prácu. Všimnite si aj úsporný spôsob písania chemických reakcií. PK Organocatalytic approach in the synthesisof natural & bioactiveproducts Martin Huťka

  2. Organic synthesis ORGANIC CHEMISTRY Target-oriented Methodology • Synthesis of target molecules • biologic active compounds • pharmaceutics • materials • Catalysis • transition metal catalysis • organocatalysis • New reactions developement • Total synthesis • natural products

  3. Ipsenol Ips latidens List B., Pojarliev P., Castello C., Org. Lett., 2001, 3, 573. Ikishima H., Sekiguchi Y., Ichikawa Y., Kotsuki H., Tetrahedron, 2006, 62, 311. Serricormin Lasioderma serricorne Ward D. E., Jheengut V., Beye G. E., J. Org. Chem., 2006, 71, 8989.

  4. (-)-CP 55940 (potential antipsychotic drug) Itagaki N., Sugahara T., Iwabuchi Y., Org. Lett., 2005, 7, 4181. Prelactone B(polyketide antibiotics precursor) Streptomyces griseus Pihko P. M., Erkkila A., Tetrahedron Lett., 2003, 44, 7607.

  5. Trichostatin A(deacetylase inhibitor, potential anticancer act., antibiotic) Streptomyces platensis Zhang S., Duan W., Wang W., Adv. Synth. Cat., 2006, 348, 1228. Convolutamydines(antibacterial) Amathia convoluta Yuan W-Ch., Zhang X-M., Cun L-F., Du X-L., Chen W-B., Tetrahedron, 2010, 66, 1441.

  6. Polyoxamic acid, Polyoxin J(antibiotics) Streptomyces cacaoi asoensis Enders D., Vrettou M., Synthesis, 2006, 2155. epi-Cytoxazone(against astma, dermatitis) streptomyces Park T-H., Kim S-G., Tetrahedron: Asymmetry, 2008, 19, 1626.

  7. Botryodiplodin(antibacterial, anticancer, antifugal, phytotoxic, mitogenic) Penicillium roqueforti Andrey O., Alexakis A., Tomassini G., Berdardinelli G., Adv. Synth. Cat., 2004, 346, 1147. Brasoside Verbena littoralis Mangion I. K., MacMillan D. W. C., J. Am. Chem. Soc., 2005, 127, 3696.

  8. D-arabino phytosphingosine, Jaspine B (Pachastrissamin) (cytotoxic against lung tumor) Pachastrissa sponge Enders D., Gasperi T., Chem. Comm., 2007, 88. Enders D., Terteryan V., Palecek J., Synthesis, 2008, 14, 2278.

  9. Mefloquine(Lariam – antimalaric) Xie Z-X, Zhang L-Z, Ren X-J, Tang S-Y, Li Y, Chin. J. Chem., 2008, 26, 1272. Propranolol, Naftopidil(antihypertensive) Kalkote U. R., Chavan S. P., Gore R. G., Panchgalle S. P., Tetrahedron: Assymetry, 2009, 20, 1767.

  10. Enterolactone (anticarcinogenic) Hajra S., Giri A. K., Hazra S., J. Org. Chem., 2009, 74, 7978. Gingerol Wang W., Duan W., Zhang S., Ma S., Bioorg. Med. Chem., 2009, 19, 3909.

  11. Linezolid(Zyvoxid, antibiotic) Duan W., Wang W., Liu W., Luo G., Li P., Zhang H., Zhang S., Chen X., Song L., Org Lett., 2008, 10, 23, 5489. Fumagilol (antibacterial, against intestinal infections) Aspergillus fumigatus Hayashy I., Osada H., Kakea H., Shoji M., Toyoshima M., Yamaguchi J., Angew. Chem. Int. Ed., 2006, 45, 789.

  12. Juvabione(insecticide, antifungal) Abies lasiocarpata Iwabuchi Y., Itagaki N., Chem. Commun., 2007, 1175.

  13. Lasubine II Lagerstroemia subcostata Reddy Ch. J., Murali R. V. N. S., Chandrasekhar S., Tetrahedron Lett. 2009, 50, 5686. (R)-6-((S)-1-hydroxyundecyl)tetrahydro-2H-pyran-2-one Culex mosquito Ikishima H., Sekiguchi Y., Ichikawa Y., Kotsuki H., Tetrahedron, 2006, 62, 311.

  14. Spiculisporic acid (detergents, gelation agents, coloring agents) Penicillinium spiculosporum Brown S. P., Goodwin N. C., MacMillan D. W. C., J. Am. Chem. Soc. , 2003, 125, 1192. Lepidopterans Christmann M., Turp D., Liu T., Julis J., Berner R., Figueiredo R. M., J. Org. Chem., 2007, 72, 2, 640.

  15. Flustramine B (muscle relaxant, antispasmodic) Flustra foliacea MacMillan D. X. C., Xiao W-J., Cinz C. J., Kim S-G., Austin J. F., Proc. Natl. Acad. Sci. USA, 2004, 1015482. Curcuphenol (antibacterial, low cytotoxic ) Kim S. G., Kim J., Jung H., Tetrahedron Lett., 2005, 46, 2437. Didictus flavus

  16. Solanapyrone D (DNA polymerase inhibitor) Alternaria solani MacMillan D. W. C., Jen W. S., Wilson R. W., J. Am. Chem. Soc., 2005, 127, 11616. Angustureine Galipea officinalis Fustero S., Moscardó J., Jiménez D., Pérez-Carrión M. D., Sánchez-Soselló M., del Pozo C., Chem. Eur. J., 2008, 14, 9868.

  17. Conicol (antibacterial, against leucemia) Hong B-Ch, Kotame P, Tsai Ch-W, Liao J-H, Org. Lett., 2010, 12, 4, 776. Aplidium conicum (2S,3R)-3-methyl-3-(4-methylpent-3-enyl)oxirane-2-carbaldehyde Jorgensen K. A., Zhuang W., Poulsen T. B., Franzen J., Marigo M., J. Am. Chem. Soc., 2005, 127, 6964.

  18. nor – Platencin (antibiotic) Streptomyces platensis Snider B.B., Rybak M.J., Rossi K. L., Barykina O. V., Org. Lett., 2009, 11, 22, 5334.

  19. Palitantin(antifungicide, antibiotic, potential HIV-1 transcriptase inhibitor) Penicillium palitans Hong B-Ch., Wu M-F., Tseng H-Ch., Huang G-F., Su Ch-F., Liao J-H., J. Org. Chem., 2007, 72, 8459

  20. Tolterodine (Detrol, Detrusitol - antimuscarinics) MacMillan D. W. C., Simmons B., Paras N. A., Tetrahedron, 2009, 65, 3232 Paroxetine(Seroxat, Paxil - antidepressant) Jorgensen K. A., Marigo M., Franzen J., Landa A., Brandau S., Angew. Chem. Int. Ed., 2006, 45, 4305.

  21. Minfiensine Strychnos nux vomica MacMillan D. W. C., Simmons B., Jones S. P., J. Am. Chem. Soc., 2009, 131, 13606.

  22. Ricciocarpin(against bilharziosis - snail fever) Ricciocorpus natans List B., Michrowska A., Nature Chem., 2009, 1, 225. Warfarin (Cumadin) (anticoagulant) Jorgensen K. A., Hansen T., Halland N., Angew. Chem. Int. Ed., 2003, 42, 4955.

  23. Hapalindol Q(antibiotic) Haplosiphon fontinalis Kerr M. A., Kinsman A. C., J. Am. Chem., Soc., 2003, 125, 14120. (R,E)-3,7,11-trimethyldodeca-6,10-dienal List B., Mayer S., Angew. Chem. Int. Ed., 2006, 45, 4193.

  24. ent-Dihydrocorynantheol (antibacterial) Mitragyna parvifolia Ohsawa A., Nagata K., Miyauchi K., Yokoya M., Itoh T., Org. Lett., 2006, 8, 1533.

  25. a-Tocopherol Woggon W-D., Chougnet A., Liu K., Angew. Chem., Int. Ed., 2008, 47, 5827.

  26. Aromadendranediol(sedative, analgetic) Sinularia mayi Xylophia brasiliensis MacMillan D. W. C., Walji A. M., Simmons B., Angew. Chem., Int. Ed., 2009, 48, 4349.

  27. Inophillium(HIV trascriptase inhibitor) Callophylum inophyllum Ishikawa T., Ikeda T., Tanaka T., Kumamoto T., Sekino E., J. Org. Chem., 2004, 69, 8, 2760.

  28. Huperzine A(acetylcholinesterase inhibitor – anti-Alzheimer drug, Chinese medicine) Hupezia serrata Terashima S., Katoh T., Yoshino T., Kaneko S., Tetrahedron, 1998, 54, 5471. Tanikolide(antifungal) Lyngbya majuscula Deng L., Liu X., Khan J., Hong R., Wu F., Angew. Chem. Int. Ed., 2006, 45, 4301.

  29. Mycestericin E Mycelia sterilia Hatakeyama S., Esumi T., Furukawa M., Iwabuchi Y., Chem. Commun., 2001, 2030.

  30. Monomorine Monomorium pharaonis Maruoka K., Kano T., Kumano T., Wang Y-G., Org. Lett., 2009, 11, 9, 2027. Galipine (antipyretic, antispasmodic) Galipea officinalis Moulis C., Fouraste I., Fabre N., Hannedouche S., Jacquemond-Collet I., Phytochem., 1999, 51, 1167.

  31. Cleroindicines Clerodendrum indicum You S. L., Zheng Ch., Rong Z-Q., Gu Q., J. Am. Chem. Soc., 2010, 132, 4056. Rolipram (antidepressant, anti-inflammatory drug) Barnes et all., J. Am. Chem. Soc., 2002, 124, 44, 13097.

  32. Pumiliotoxin C (neurotoxic) Dendrobates tinctorius Rueping M., Antonchick A. P., Angew. Chem. Int. Ed., 2007, 46, 4562.

  33. Epibatidine(analgesic) Epipedobates tricolor Takemoto Y., Yabuta T., Hoashi Y., Tett. Lett., 2004, 45, 9185. Dihydrokawain (Marindinin) Piper methysticum Ding K., Zhao D., Du H., Chem. Eur. J., 2004, 10, 5964.

  34. Glabrescol Spathelia glabrescens Corey E. J., Xiong Z., J. Am. Chem. Soc., 2000, 122, 9328.

  35. Roseophilin(antibiotic) Streptomyces griscovirides Tius M. A., Harrington P. E., J. Am. Chem. Soc., 2001, 123, 35, 8509.

  36. The End

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