The pursuit of polyketide structures for anticancer, antifungal, and antibiotic purposes has a rich history of discovery of novel synthetic methods.  Among the most common synthons and late-stage intermediates are aldehydes, which can be synthetically coupled to other fragments through a rich array of transformations.  In an effort to add to the diversity of available transformations we report progress on a coupling reaction to establish the common 1,3,5-polyoxygenation pathway with regio- and stereochemical specificity.  This process utilizes two unique aldehydes as putative late-stage intermediates and provides an orthogonal protection scheme <i>in situ</i>.  This poster discusses initial work to define the chemical space of the coupling reaction and address issues around its catalytic abilities and alcohol protection.

Progress toward a lynchpin reaction for polyketide total synthesis

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