Synthesis of (+)-(1S, 4R)-1-(1-chlorovinyl)-7, 7-dimethyl-bicyclo [2.2. 1] heptan-2-one

…, VZ Vasikov, LV Spirikhin, MS Miftakhov

Index: Vostrikov; Vasikov; Spirikhin; Miftakhov Russian Journal of Organic Chemistry, 2004 , vol. 40, # 9 p. 1371 - 1372

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Abstract

7, 7-Dimethyl-1-vinylbicyclo [2.2. 1] heptan-2-one (I) which is readily accessible from d- camphorsulfonic acid [1] is extensively used in the synthesis of taxoids [2, 3] and their precursors [4]. No specific chemical properties of keto olefin I have been noted; for example, by the action of deprotonating agents it gives rise to expected enolates which are involved in reactions typical of such derivatives [5, 6]. While trying to effect Michael reaction of methyl ...