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.
Muratore
Agnès
A
Laboratoire de Recherche, V. Mane & Fils, 620, route de Grasse, FR-06620 Le Bar-sur-Loup.
Clinet
Jean-Claude
JC
Duñach
Elisabet
E
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