Abstract
Total synthesis of the proposed structure of torrubiellutin C has been successfully achieved. The synthesis started with steric inversion of a hydroxyl group in a skipped dienoate, which can be easily prepared by SN2′ reaction of epoxydienoate with borane. Thereafter, several carbon elongations and acyclic stereocontrols afforded a polyketide moiety. Esterification of the polyketide moiety with N-methyl-l-phenylalanine derivative and the subsequent macrolactamization generated the proposed structure. The spectroscopic data considerably disagreed with them of natural product.
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