Abstract
High selectivity (82 %) to 3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol, a potent anti-Parkinson drug, was achieved in the isomerization of verbenol oxide at the conversion level of 96 % in N,N-dimethylacetamide at 140 °C over a metal modified zeolite, Fe-Beta-300 with SiO2 to Al2O3 ratio of 300. This catalyst exhibits both weak and medium strong Brønsted and Lewis acid sites.
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References
Lajunen MK, Maunula T, Koskinen AMP (2000) Tetrahedron 56:8167–8171
Ardashov OV, Pavlova AV, Il’ina IV, Morozova EA, Korchagina DV, Karpova EV, Volcho KB, Tolstikova TG, Salakhutdinov NF (2011) Highly potent activity of (1R,2R,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex3-ene-1,2-diol in animal models of Parkinson’s disease. J Med Chem 54:3866–3874
Kim H, Su L, Jung H, Koo S (2011) Selective deoxygenation of allylic alcohol: stereocontrolled synthesis of lavandulol. Org Lett 13:2682–2685
Il′ina IV, Volcho KP, Korchagina DV, Barkhash VA, Salakhutdinov NF (2007) Reactions of allyl alcohols of the pinane series and of their epoxides in the presence of montmorillonite clay. Helv Chim Acta 90:353–368
Ardashov OV, Il’ina IV, Korchagina DV, Volcho KP, Salakhutdinov NF (2007) Unusual α-hydroxyaldehyde with a cyclopentane framework from verbenol epoxide. Mendeleev Commun 17:303–305
Il’ina IV, Kurbakova SY, Volcho KP, Salakhutdinov NF (2010) Effect of nature of exchange cations in montmorillonite clay on the direction of verbenol epoxide transformations. Chem Sustain Dev 18:377–380
Amri H, El Gaied MM, Hirsi M (1983) Reaction of trimethylamine dihydrofluoride with simple epoxides and α-functionalized derivatives of bicyclo 3.1.1. Heptanemonoterpene. J Soc Chim Tunis 10:25–32
Volcho KP, Il`ina IV, Salakhutdinov NF, Anikeev VI (2011) Rearrangements of verbenol epoxide in supercritical fluids. Arkivoc Viii:134–140
Fernandez-Mateos A, Teijon PH, Gonzalez RR (2011) Radical reactions on pinene-oxide derivatives induced by Ti(III). Tetrahedron 67:9529–9534
Kumar N, Mäki-Arvela P, Faten Diaz S, Aho A, Demidova Y, Linden J, Shepidchenko A, Tenho M, Salonen J, Laukkanen P, Laskhul A, Dahl J, Sinev I, Leino AR, Kordas K, Salmi T, Murzin DYu (2013) Isomerization of α-pinene oxide over iron-modified zeolites. Topics Catal 56:696–713
Kumar N, Leino E, Mäki-Arvela P, Aho A, Käldström M, Tuominen M, Laukkanen P, Eränen K, Mikkola JP, Salmi T, Murzin DYu (2012) Synthesis and characterization of solid base mesoporous and microporous catalysts: influence of support, structure and type of base metal. Micropor Mesop Mater 152:71–77
Stekrova M, Kumar N, Mäki-Arvela P, Ardashov OV, Volcho KP, Salakhutdinov NF, Murzin DYu (2013) Selective preparation of trans-carveol over ceria supported mesoporous materials MCM-41 and SBA-15. Materials 6:2103–2118
Acknowledgments
This work is part of the activities at the Åbo Akademi University, Process Chemistry Centre within the Finnish Centre of Excellence Program appointed by the Academy of Finland. The publication was supported by the UniCRE project, funded by the EU Structural Funds and the state budget of the Czech Republic.
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Stekrova, M., Kumar, N., Mäki-Arvela, P. et al. Opening of monoterpene epoxide to a potent anti-Parkinson compound of para-menthane structure over heterogeneous catalysts. Reac Kinet Mech Cat 110, 449–458 (2013). https://doi.org/10.1007/s11144-013-0615-9
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DOI: https://doi.org/10.1007/s11144-013-0615-9