Taumycin is a novel, macrocyclic marine-derived secondary metabolite with promising biological activity and reported cytotoxicity to the UT-7 leukemic cell line.Due to its low isolation yield, extensive biological evaluation has not yet been performed, and the mechanism of action of this macrolide remains unknown. We became interested in this natural product because of its unique molecular architecture and biosynthetic origin from two distinct molecular pathways. We have designed an efficient synthesis of Taumycin that relies on a thermally catalyzed dioxinone rearrangement as the critical macrocyclization step. To the best of our knowledge this ring closing strategy is yet untried in the field of depsipeptide total synthesis, and represents a new strategy for depsipeptide ring construction. We now report our progress directed towards the first total synthesis of taumycin aldehyde, a known degradation product. Efforts in this area are currently being applied towards the synthesis of the parent natural compound.

Synthetic studies towards the total synthesis of taumycin

245th National Meeting (2013)

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