SIA7248 is a recently discovered 60-membered polyketide dimer isolated from marine Streptomyces spp. A7248. Its analogs have been shown to have potent biological activity against methicillin-resistant Staphylococcus aureus (MRSA). SIA7248 is a symmetric dimer comprised of two 1,3-syn-tetraol segments, which intrigued us to use an iterative hydration of polyenes approach for its synthesis. A key step in our synthesis is the application of the Leighton allylation to diastereoselectively install a second 1,3-syn-diol fragment. In this regard, we study the effects of metal chelation in the allylation of benzylidene protected syn-3,5-dihydroxyaldehydes. Our results suggest that the type and stoichiometry of chelating metals present in the reaction can have a profound affect on the steroeselectivity of the allylation. Our latest results along these lines will be presented.

Optimization of the Leighton allylation of aldehydes: Application for the synthesis of SIA7248

251st National Meeting (2016)

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