Journal of Organic Chemistry 2004-07-09

Total synthesis of zincophorin and its methyl ester.

Magali Defosseux, Nicolas Blanchard, Christophe Meyer, Janine Cossy

Index: J. Org. Chem. 69 , 4626-4647, (2004)

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Abstract

A total synthesis of the naturally occurring ionophore zincophorin has been realized. The route features an intramolecular oxymercuration of a cyclopropanemethanol and a Carroll-Claisen rearrangement for the respective elaboration of the C1-C12 and C13-C25 subunits, which have been assembled by using a highly diastereoselective titanium-mediated aldol condensation.