Metals debenzylation of tetrazoles, and high convergent straightforward stereoselective synthesis of (+)-C(9a)-Epiepiquinamide.

Abstract

This manuscript encloses two principal parts: In the first part, We report the use of three metals for debenzylation of protected tetrazoles: indium, magnesium and zinc, comparing the process of using metals, and taking into account financial aspects, the use of zinc show to be the most effective for substrates non-sensitive to acidic conditions. For substrates sensitive to acid, magnesium or indium metal can be used, can we say that zinc being preferable considering reaction conditions and metal prices. In the second part, We have synthesis from commercially available compounds, the (+)-C(9a)- epiepiquinamide the reaction was carried out in six synthetic operations starting from a diastereoselective aza-Henry reaction of a chiral N-tert-butanesulfinyl imine and ethyl 4- nitrobutanoate, the configuration of the sulfur atom of the sulfinyl group determining the configuration of C(9a) stereocenter in this transformation.