title: An expedient synthesis of linden ether.
abstract: We here describe a comprehensive study on the preparation of the intensive flavor 3,9-epoxy-p-mentha-1,4(8)-diene (1). Key steps of the presented synthesis are the selective addition of MeLi to the keto-ester 7, the regioselective cyclization of the obtained triol to give the ethers 4 and 8 and the selective dehydration of ether 4 through the use of POCI3 and pyridine. It is worth noting that the presented synthesis represents the first expedient and reliable entry to ether 1. Being present in linden honey, 1 is also known as linden ether and it has been regarded as a potential marker for the authentication of the linden honey origin. Therefore, ether 1 can be used as a useful reference standard for the analysis of the natural flavors, as we demonstrated by means of its identification in a sample ofunifloral linden honey.
authors.forename: Stefano
authors.initials: S
authors.lastname: Serra
authors.forename: Alessandra A
authors.initials: AA
authors.lastname: Cominetti
mesh_terms: D006722:Honey / Q000032:analysis; D039821:Monoterpenes / Q000032:analysis / Q000138:chemical synthesis*; D032384:Tilia / Q000737:chemistry*
chemical_list: C588153:3,9-epoxy-p-mentha-1,4(8)-diene; D039821:Monoterpenes