Asymmetric Total Synthesis of C9'-epi-Sinefungin [post]

Ludovic Decultot, Rocco L. Policarpo, Brandon Wright, Danny Huang, Matthew Shair
2020 unpublished
The natural nucleoside (+)-sinefungin, structurally similar to cofactor S-adenosyl-L-methionine (SAM), 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
more » ... dification is highlighted, opening an avenue for the discovery of new MTs inhibitors.
doi:10.26434/chemrxiv.12318797.v1 fatcat:5wskniax4zeb7opvll6hqqzm4u