Molecules
Luka Ciber, Tjaša Koželj, Kaja Prosenak, Nejc Petek, Franc Požgan, Jurij Svete, Bogdan Štefane and Uroš Grošelj
(+)-Isocampholenic acid, prepared in two steps from (1S)-(+)-10-camphorsulfonic acid in 60% yield (on a 172 mmol scale), served as the starting compound for the synthesis of small libraries of isocampholenic acid derivatives, comprising a total of 60 compounds, which are of interest for their olfactory properties. Although isocampholenic acid derivatives are thermodynamically up to 5.9 kcal/mol less stable than endocyclic alkene isomers according to DFT calculation, only minor (up to 2 %) isomerization to α-campholenic acid isomers was observed in most cases. The products were fully characterized and their odor properties were preliminarily assessed by untrained layman. This study provides the first systematic exploration of the chemical space of isocampholenic acid, revealing novel derivatives with distinctive olfactory profiles and identifying promising directions for future functionalization aimed at fragrance development.
Read article: Molecules, 2025, 30, 3794
