Synthesis of new exo- and endo-3,8-dihydro-beta-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 beta-santalol. In particular, exo- and endo-3,8-dihydro-beta-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.
Laboratoire de Recherche, V. Mane & Fils, 620, route de Grasse, FR-06620 Le Bar-sur-Loup.
Agnès
A
Muratore
Jean-Claude
JC
Clinet
Elisabet
E
Duñach
D000438:Alcohols / Q000138:chemical synthesis / Q000737:chemistry*; D000081223:Polycyclic Sesquiterpenes; D032123:Santalum / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis / Q000737:chemistry*; D012903:Smell; D013237:Stereoisomerism
D000438:Alcohols; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; C043206:santalol