Synthetic efforts toward the total synthesis of sanctolide A and C2-epimer of sanctolide A are presented. Sanctolide A belongs to a relatively rare class of polyketide non-ribosomal peptide (PK-NRP) hybrids that was isolated from a moderately cytotoxic cell extract of cyanobacterium Oscillatoria sancta (SAG 74.79). The 14-membered macrolide which posses an uncommon N-methyl enamide chain was shown to have promising biological activity (moderate cytotoxicity in brine shrimp toxicity assay, 23.5 mM). Our progress towards the synthesis of the titled natural product, simpler analogues and studies geared to the understanding of the reactivity of this class of natural products will also be presented.

Efforts towards the total synthesis of sanctolide A and the C2-epimer of sanctolide A

254th National Meeting (2017)

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