Biomimetic Synthesis of Nor-Cedrene and Nor-Isozizaene Sesquiterpenoids and Exploration of Their Olfactive Properties

We report the preparation of nor-bisabolyl epoxide 13 and its use as a common biomimetic intermediate for the synthesis of nor-sesquiterpenoids. Through a cationic cyclization cascade pathway, we prepared nor-isozizaenol 25, ultimately constituting an eight-step access to this complex sesquiterpenoid from inexpensive and abundant starting materials. Using a radical cyclization cascade pathway, we prepared nor-cedryl alcohol 26 from the same intermediate. Derivatization of these two products led to the discovery of two potent woody odorants of interest in perfumery.

Automated summary

We report the preparation of nor-bisabolyl epoxide 13 and its use as a common biomimetic intermediate in the synthesis of nor-sesquiterpenoids. By employing different cascade reactions, nor-isozizaenol and nor-cedryl alcohol were obtained from the same intermediate, leading to the discovery of two potent woody odorants with significance in perfumery.