Total synthesis of Stambomycin D Validated Modular Polyketide Synthase-Based Stereochemical Assignment

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Stambomycins A-D are macrolide antibiotics with promising antitumor activity, identified as metabolites of Streptomyces ambofaciens. Aside from two stereocenters installed through cytochrome P450 oxidations, their stereochemistry has been predicted by sequence analysis of the polyketide synthase. We proposed the first total synthesis of Stambomycin D to elucidate the unknown two stereocenter and validate the predicted assignment, which will be a significant development in the structural determination of natural products.