Isomerization of bicyclic terpene epoxides into allylic alcohols without changing of the initial structure

Yulia Demidova; OV Ardashov; OA Simakova; Olga Simakova; KP Volcho; NF Salakhutdinov; Dmitry Murzin

doi:10.1016/j.carbon.2014.05.015

Isomerization of bicyclic terpene epoxides into allylic alcohols without changing of the initial structure

Yulia Demidova, OV Ardashov, OA Simakova, Olga Simakova, KP Volcho, NF Salakhutdinov, Dmitry Murzin

Research output: Contribution to journal › Article › Scientific › peer-review

54 Citations (Scopus)

Abstract

A novel method of (1S,2R,3R,5R)-6,6-dimethy1-4-methylenebicyclo[3.1.1]heptane-2,3-diol synthesis, which is a valuable intermediate in the synthesis of a perspective potent anti-Parkinson drugs, in the presence of TiO2 was proposed. Catalytic activity of TiO2 in the bicyclic terpene epoxides isomerization to corresponding allylic alcohols without changing of the initial structure was demonstrated, contrary to titania-supported Au catalysts which promoted rearrangement with predominant formation of a cyclopentene alpha-hydroxy ketone.

Original language	Undefined/Unknown
Pages (from-to)	162–166
Journal	Journal of Molecular Catalysis A: Chemical
Volume	388-389
DOIs	https://doi.org/10.1016/j.carbon.2014.05.015
Publication status	Published - 2014
MoE publication type	A1 Journal article-refereed

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10.1016/j.carbon.2014.05.015

Cite this

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title = "Isomerization of bicyclic terpene epoxides into allylic alcohols without changing of the initial structure",

abstract = "A novel method of (1S,2R,3R,5R)-6,6-dimethy1-4-methylenebicyclo[3.1.1]heptane-2,3-diol synthesis, which is a valuable intermediate in the synthesis of a perspective potent anti-Parkinson drugs, in the presence of TiO2 was proposed. Catalytic activity of TiO2 in the bicyclic terpene epoxides isomerization to corresponding allylic alcohols without changing of the initial structure was demonstrated, contrary to titania-supported Au catalysts which promoted rearrangement with predominant formation of a cyclopentene alpha-hydroxy ketone.",

author = "Yulia Demidova and OV Ardashov and OA Simakova and Olga Simakova and KP Volcho and NF Salakhutdinov and Dmitry Murzin",

year = "2014",

doi = "10.1016/j.carbon.2014.05.015",

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volume = "388-389",

pages = "162–166",

journal = "Journal of Molecular Catalysis A: Chemical",

issn = "1381-1169",

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TY - JOUR

T1 - Isomerization of bicyclic terpene epoxides into allylic alcohols without changing of the initial structure

AU - Demidova, Yulia

AU - Ardashov, OV

AU - Simakova, OA

AU - Simakova, Olga

AU - Volcho, KP

AU - Salakhutdinov, NF

AU - Murzin, Dmitry

PY - 2014

Y1 - 2014

N2 - A novel method of (1S,2R,3R,5R)-6,6-dimethy1-4-methylenebicyclo[3.1.1]heptane-2,3-diol synthesis, which is a valuable intermediate in the synthesis of a perspective potent anti-Parkinson drugs, in the presence of TiO2 was proposed. Catalytic activity of TiO2 in the bicyclic terpene epoxides isomerization to corresponding allylic alcohols without changing of the initial structure was demonstrated, contrary to titania-supported Au catalysts which promoted rearrangement with predominant formation of a cyclopentene alpha-hydroxy ketone.

AB - A novel method of (1S,2R,3R,5R)-6,6-dimethy1-4-methylenebicyclo[3.1.1]heptane-2,3-diol synthesis, which is a valuable intermediate in the synthesis of a perspective potent anti-Parkinson drugs, in the presence of TiO2 was proposed. Catalytic activity of TiO2 in the bicyclic terpene epoxides isomerization to corresponding allylic alcohols without changing of the initial structure was demonstrated, contrary to titania-supported Au catalysts which promoted rearrangement with predominant formation of a cyclopentene alpha-hydroxy ketone.

U2 - 10.1016/j.carbon.2014.05.015

DO - 10.1016/j.carbon.2014.05.015

M3 - Artikel

SN - 1381-1169

VL - 388-389

SP - 162

EP - 166

JO - Journal of Molecular Catalysis A: Chemical

JF - Journal of Molecular Catalysis A: Chemical

ER -