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Digitale Medien

Synthese von rac-Norartemeseol (1991)

Kirschning, Andreas ; Narjes, Frank ; Schaumann, Ernst

Weinheim : Wiley-Blackwell

Liebigs Annalen 1991 (1991), S. 933-936

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Details

ISSN: 0170-2041

Schlagwort(e): Norartemeseol, rac- ; Allyl anion, hetero-substituted ; Oxiranes, ring-opening ; Tetrahydrofuran, substituted ; Cyclopropane, vinyl- ; Chemistry ; Organic Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: Synthesis of rac-NorartemeseolThe synthesis of the terpenoid rac-norartemesol (1b) is accomplished using epoxide ring-opening reactions as key steps. Thus, addition of the thio-substituted allyl anion 2b to ethylene oxide followed by proton-induced cyclisation provides the tetrahydrofuran 4a. The oxirane 6, which is formed by simple functional group interconversion, is opened by the diethylaluminium salt 10 of a propargylsilane. After catalytic hydrogenation and tosylation, fluoride-induced cyclisation of the allylsilane 13 gives the target molecule 1b.

Materialart: Digitale Medien

URL: http://dx.doi.org/10.1002/jlac.1991199101159

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