The
natural nucleoside (+)-sinefungin, structurally similar to
cofactor S-adenosyl-l-methionine,
inhibits various SAM-dependent methyltransferases (MTs). Access to
sinefungin analogues could serve as the basis for the rational design
of small molecule methyltransferase inhibitors. We developed a route
to the unnatural C9′ epimer of sinefungin that employed a diastereoselective
Overman rearrangement to install the key C6′ amino stereocenter.
The ability for late-stage modification is highlighted, opening an
avenue for the discovery of new MT inhibitors.
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Decultot, Ludovic; Policarpo, Rocco L.; Wright, Brandon A.; Huang, Danny; Shair, Matthew D. (2020). Asymmetric Total Synthesis of C9′-epi-Sinefungin. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.0c01956