Biomimetic Synthesis of Nor‐Cedrene and Nor‐Isozizaene Sesquiterpenoids and Exploration of Their Olfactive Properties. Issue 46 (27th June 2022)

• Record Type: Journal Article
• Authors: Georgiev, Tony; Armanino, Nicolas
• Is Part Of: Chemistry. Volume 28:Issue 46(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-06-27
• Subjects: biomimetic synthesis -- cationic cyclization -- fragrances -- radical cyclization -- terpenes; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.202201037
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: 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. Abstract : The chemical synthesis of isozizaene‐ and cedrene‐type nor‐sesquiterpenoids from a simple bio‐inspired precursor nor‐bisabolyl epoxide is described. This key intermediate undergoes selective cyclization cascades without the need for enzymatic control. By choosing cationic or radical cyclization conditions, each sesquiterpene scaffold could be prepared selectively and led to the discovery of new woody odorants of perfumery interest.