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...

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Veröffentlicht in:	Journal of natural products (Washington, D.C.) D.C.), 2004-02, Vol.67 (2), p.189-193
Hauptverfasser:	Cerda-García-Rojas, Carlos M, Bucio, María A, Román, Luisa U, Hernández, Juan D, Joseph-Nathan, Pedro
Format:	Artikel
Sprache:	eng
Schlagworte:	Alicyclic compounds, terpenoids, prostaglandins, steroids Chemistry Exact sciences and technology Hydrolysis Models, Molecular Molecular Conformation Molecular Structure Odorants Organic chemistry Preparations and properties Sesquiterpenes - chemical synthesis Sesquiterpenes - chemistry Stereoisomerism Terpenoids
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Zusammenfassung:	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.
ISSN:	0163-3864 1520-6025
DOI:	10.1021/np030354e