Preparation of moreliane-derived volatile sesquiterpenes.
A series of six volatile sesquiterpenes (9-13 and 15) was prepared by thioketalization of (4R,5S,9S,10S,11S)-morel-2-en-1,7-dione (2) and of (4R,5S,7R,9R,11R)-moreli-2,10-dien-7-ol-1-one (3), followed by Raney-nickel desulfurization. The structures of the new substances were determined by 1D and 2D NMR including COSY, NOESY, HSQC, and HMBC experiments. The geometry of (3S,4R,5R,9S,10R,11S)-morelian-7-one (11), which exhibited an intense woody odor, was calculated by density functional theory at the B3LYP/6-31G level.
Departamento de Química, Centro de Investigación y de Estudios Avanzados del Instituto Politécnico Nacional, Apartado 14-740, México, D. F., 07000 Mexico. ccerda@mail.cinvestav.mx
Carlos M
CM
Cerda-García-Rojas
María A
MA
Bucio
Luisa U
LU
Román
Juan D
JD
Hernández
Pedro
P
Joseph-Nathan
D006868:Hydrolysis; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D009812:Odorants; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D012717:Sesquiterpenes; C410907:longipinene