Polypropionates are important subunits in many macrolide natural products, having a wide range of biological and medicinal activity. Their structure is characterized by an alternating sequence of methyl and hydroxy groups in an aliphatic chain having a specific configuration. Since these fragments have high levels of stereochemical information, the control of the stereoselectivity is key to the synthetic approach. Currently, our laboratory efforts are focused in the development of a reiterative epoxide-based methodology for the synthesis of these structures. We are specifically working on the regioselective cleavage of cis- and trans-2-methyl-3,4-epoxy alcohols as precursors to the first stereotetrad. This methodology gives us access to the different stereochemical relationships that are present in these units. We are using this approach for the synthesis of polypropionate fragments, which are present in ansamycin antibiotics, including, chaxamcyn A and D, salinisporamycin, rifamycin, among others.

Epoxide-based methodology for the synthesis of stereotetrads: Application to the synthesis of propionate fragments

245th National Meeting (2013)

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