Synthesis and olfactory evaluation of spiro tricyclic diether structures

Readily available dienols were efficiently synthesised and cycloisomerised using a low catalyst loading of bismuth(III) triflate on the gram‐scale. Appealing complex tricyclic structures featuring a spirocyclic ether motif were obtained in very good yields. The olfactory properties of these original...

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Bibliographic Details
Published in:Flavour and fragrance journal 2017-03, Vol.32 (2), p.119-125
Main Authors: Ondet, Pierrick, Plessis, Caroline, Lemière, Gilles, Duñach, Elisabet
Format: Article
Language:English
Subjects:
Bismuth
Catalysts
Chemical synthesis
cyclisation
odour evaluation
Olfactory properties
spirocycle
tricyclic diether
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Summary:Readily available dienols were efficiently synthesised and cycloisomerised using a low catalyst loading of bismuth(III) triflate on the gram‐scale. Appealing complex tricyclic structures featuring a spirocyclic ether motif were obtained in very good yields. The olfactory properties of these original compounds has been assessed and pleasant fresh and woody notes from moderate to high intensity were noticed. In general, 2‐oxanorbornane compounds possess woody notes whereas analogous 7‐oxanorbornanes present greener tonalities. Copyright © 2016 John Wiley & Sons, Ltd. Readily available dienols were efficiently synthesised and cycloisomerised using a low catalyst loading of bismuth (III) triflate on the gram‐scale. Appealing complex tricyclic structures featuring a spirocyclic ether motif were obtained in very good yields. The olfactory properties of these original compounds has been assessed and pleasant fresh and woody notes from moderate to high intensity were noticed. In general, 2‐oxanorbornane compounds possess woody notes whereas analogous 7‐oxanorbornanes present greener tonalities.
ISSN:0882-5734
1099-1026
DOI:10.1002/ffj.3361