title: Lactones. 21. Synthesis and odoriferous properties of lactones with the p-menthane system.
abstract: Starting from (R)-(+)- and (S)-(-)-pulegone, enantiomeric pairs of esters and lactones with the p-menthane system were obtained. The Claisen rearrangement of allylic alcohols and iodolactonization of gamma,delta-unsaturated acids were the key steps of syntheses presented. The structures of compounds were determined by both spectroscopic and crystallographic methods. Some of the synthesized compounds are characterized by interesting odoriferous properties.
authors.affiliation: Department of Chemistry, Agricultural University, Norwida 25, 50-375 Wrocław, Poland. iwa_dams@ozi.ar.wroc.pl
authors.forename: Iwona
authors.initials: I
authors.lastname: Dams
authors.forename: Agata
authors.initials: A
authors.lastname: Bialoniska
authors.forename: Zbigniew
authors.initials: Z
authors.lastname: Ciunik
authors.forename: Czesław
authors.initials: C
authors.lastname: Wawrzenczyk
mesh_terms: D018360:Crystallography, X-Ray; D000081005:Cyclohexane Monoterpenes; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D027541:Mentha / Q000737:chemistry; D015394:Molecular Structure; D039821:Monoterpenes; D009812:Odorants / Q000032:analysis*; D009822:Oils, Volatile / Q000737:chemistry; D013237:Stereoisomerism; D013729:Terpenes
chemical_list: D000081005:Cyclohexane Monoterpenes; D007783:Lactones; D039821:Monoterpenes; D009822:Oils, Volatile; D013729:Terpenes; C039648:pulegone; C409815:mintlactone