Heterogeneous catalysis for transformation of biomass derived compounds beyond fuels: Synthesis of monoterpenoid dioxinols with analgesic activity

Heterogeneous catalysis for transformation of biomass derived compounds beyond fuels: Synthesis of monoterpenoid dioxinols with analgesic activity Full article

Journal

Journal of Molecular Catalysis A: Chemical
ISSN: 1381-1169

Output data

Year: 2015, Volume: 397, Pages: 48-55 Pages count : DOI: 10.1016/j.molcata.2014.10.023

Tags

Zeolite; Addition; Terpenoid; Dioxinol

Authors

Torozova Alexandra ¹ , Maki-Arvela Paivi ¹ , Aho Atte ¹ , Kumar Narendra ¹ , Smeds Annika ¹ , Peurla Markus ² , Sjoholm Rainer ¹ , Heinmaa Ivo ³ , Korchagina Dina V. ⁴ , Volcho Konstantin P. ^4,5 , Salakhutdinov Nariman F. ^4,5 , Murzin Dmitry Yu. ¹

Affiliations

1	(Данные Web of science) Abo Akad Univ, Proc Chem Ctr, SF-20500 Turku, Finland
2	(Данные Web of science) Univ Turku, Turku, Finland
3	(Данные Web of science) Inst Chem Phys & Biophys, Tallinn, Estonia
4	(Данные Web of science) Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia
5	(Данные Web of science) Novosibirsk State Univ, Novosibirsk 630090, Russia

Catalytic synthesis of a dioxinol compound, (2S,4aR,8R,8aR)-4,4,7-trimethyl-2-phenyl-4a,5,8,8a-tetrahydro-4H-benzo[d][1,3]dioxin-8-ol, exhibiting analgesic activity was demonstrated over Femodified beta zeolite. During interactions between cis-verbenol oxide and benzaldehyde, two main reactions occurred. In the first reaction, namely isomerization of verbenol oxide both cyclopentenic hydroxyketone, oxetane as well as a cyclohexyl compound, (1R,2R,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol were formed. In the second parallel reaction the target compound was generated. The highest yield of the target compound was achieved in the reaction between verbenol oxide and benzaldehyde at their molar ratio of 1:133 with the bifunctional iron modified Fe-H-Beta-150 catalyst at 70 degrees C giving a much higher yield than reported earlier in the literature, being 46 mol-% at complete conversion of verbenol oxide. (C) 2014 Elsevier B.V. All rights reserved.

Torozova A. , Maki-Arvela P. , Aho A. , Kumar N. , Smeds A. , Peurla M. , Sjoholm R. , Heinmaa I. , Korchagina D.V. , Volcho K.P. , Salakhutdinov N.F. , Murzin D.Y.
Heterogeneous catalysis for transformation of biomass derived compounds beyond fuels: Synthesis of monoterpenoid dioxinols with analgesic activity
Journal of Molecular Catalysis A: Chemical. 2015. V.397. P.48-55. DOI: 10.1016/j.molcata.2014.10.023 WOS Scopus

Published print:

Feb 1, 2015

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