Synthesis and olfactory properties of Phantolide analogues in racemic and optically active forms

The racemates, (+)- and (–)-enantiomers, of eight novel Phantolide analogues, which are non-natural musk odorants, were synthesized. The key step of the asymmetric synthesis was the lipase-catalysed enantioselective transesterification of a racemic primary alcohol, and the resultant two enantiomers of the primary alcohol were used as intermediates for further transformations. The odour profiles of all of the synthesized Phantolide analogues were evaluated. Some interesting findings on the odour profiles of the analogues are reported here.