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Preparation and application of (+)-(3,3-dimethyl-2-methylenenorbornan-1-yl)methyl methanesulfonate: a new and versatile chiral fenchone analogue
Authors:Te-Fang Yang  Hou-Hsun ChaoYi-Hsuan Lu  Cheng-Jung Tsai
Affiliation:Department of Applied Chemistry, Chaoyang University of Technology, Wufeng, 413 Taichung, Taiwan, ROC
Abstract:The preparation of (+)-(3,3-dimethyl-2-methylenenorbornan-1-yl)methyl methanesulfonate (9) was carried out in 2 steps, dihydroxylation and mesylation, from (−)-2-methylenebornane. Hydrolysis and reduction of 9 gave a fenchyl alcohol (2) and a methylenefenchone (21), respectively. Oxidation of 9 afforded a new analogue (23) of the class of oxatricyclo compounds. Treatment of 9 with NBS resulted in a Wagner-Meerwein rearrangement to produce brominated methylenebornane derivatives (25 and 26), which are also new compounds.
Keywords:methylenenorbornane   fenchone analogue
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