Rearrangement of Epoxide Derivatives Semisynthesized from β-Himachalene using Lewis and Bronsted Acids Catalysis

The acid-catalyzed rearrangement of epoxides 3a , 4a , 6a , and 7a derived from β-himachalene, the major constituent of Cedrus atlantica essential oil, has been studied using various Lewis and Bronsted acids. Several new enantiomerically pure ketones were obtained in good yields and high selectiviti...

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Bibliographic Details
Published in:Chemistry of natural compounds 2020-07, Vol.56 (4), p.663-669
Main Authors: Dakir, Mohamed, Elhad, Mustapha Ait, Oukhrib, Abdelouahd, Mazoir, Noureddine, Benharref, Ahmed
Format: Article
Language:English
Subjects:
Essential oils
Ketones
Medicine
NMR
Nuclear magnetic resonance
Organic Chemistry
Pharmacy
Plant Sciences
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Summary:The acid-catalyzed rearrangement of epoxides 3a , 4a , 6a , and 7a derived from β-himachalene, the major constituent of Cedrus atlantica essential oil, has been studied using various Lewis and Bronsted acids. Several new enantiomerically pure ketones were obtained in good yields and high selectivities. All products obtained were fully characterized by 1 H and 13 C NMR, and the mechanistic explanations for their formation were proposed.
ISSN:0009-3130
1573-8388
DOI:10.1007/s10600-020-03116-w