Lactones. 21. Synthesis and odoriferous properties of lactones with the p-menthane system.
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.
Dams
Iwona
I
Department of Chemistry, Agricultural University, Norwida 25, 50-375 Wrocław, Poland. iwa_dams@ozi.ar.wroc.pl
Bialoniska
Agata
A
Ciunik
Zbigniew
Z
Wawrzenczyk
Czesław
C
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
D000081005:Cyclohexane Monoterpenes; D007783:Lactones; D039821:Monoterpenes; D009822:Oils, Volatile; D013729:Terpenes; C039648:pulegone; C409815:mintlactone