Synthesis of New exo- and endo-3,8-Dihydro-β-santalols and Other Norbornyl-Derived Alcohols

Several new and differently functionalized cis‐2,3‐dimethylnorbornane derivatives presenting diverse side‐chain lengths were prepared, the structures of which are related to the natural fragrance β‐santalol. In particular, exo‐ and endo‐3,8‐dihydro‐β‐santalols, with either (E) or (Z) CC‐bond config...

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Bibliographic Details
Published in:Chemistry & biodiversity 2010-03, Vol.7 (3), p.623-638
Main Authors: Muratore, Agnès, Clinet, Jean-Claude, Duñach, Elisabet
Format: Article
Language:English
Subjects:
Alcohols - chemical synthesis
Alcohols - chemistry
Fragrances
Norbornyl derivatives
Santalols
Santalum - chemistry
Sesquiterpenes - chemical synthesis
Sesquiterpenes - chemistry
Smell
Stereoisomerism
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Summary:Several new and differently functionalized cis‐2,3‐dimethylnorbornane derivatives presenting diverse side‐chain lengths were prepared, the structures of which are related to the natural fragrance β‐santalol. In particular, exo‐ and endo‐3,8‐dihydro‐β‐santalols, with either (E) or (Z) CC‐bond configuration on the side chain, were synthesized in seven steps and 21–24% overall yields. Several other exo‐ and endo‐norbornyl alcohols with shorter side chains were also prepared in high yields. The olfactory evaluation indicated woody, sandalwood, as well as fruity notes for some of the derivatives.
ISSN:1612-1872
1612-1880
DOI:10.1002/cbdv.200900119