ISSN:
0170-2041
Keywords:
Norartemeseol, rac-
;
Allyl anion, hetero-substituted
;
Oxiranes, ring-opening
;
Tetrahydrofuran, substituted
;
Cyclopropane, vinyl-
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1991199101159
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