Add time:08/14/2019         Source:sciencedirect.com

An enantioselective approach to the synthesis of the hexahydronaphthalene nucleus of natural compactin is described. The key elements of the synthesis are as follows: (i) the preparation of the chiral starting material through enzymatic resolution of the readily available cis 2-methyl-4-oxocyclohexane carboxylic acid, (ii) conversion into the suitably protected (4S,5S)4-hydroxymethyl-5-methyl-2-cyclohexen-2-one by regioselective introduction of the α,β-carbon-carbon double bond by Pd(II)-catalyzed dehydrosilylation, (iii) construction of the new six-membered ring into the preexisting carbon skeleton using 2-(3-nitropropyl)-1,3-dioxolane as a four carbon bifunctional annelating reagent (iv) elaboration of the derived hexahydronaphthalenone to an advanced precursor already taken to the natural target by functional group manipulation, including conversion of the nitro group to the oxygenated function at C-1 and dehydration of an allylic alcohol to the required 1,3-diene moiety.

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