Asymmetric Total Synthesis of C9'- epi -Sinefungin.
ORGANIC LETTERS(2020)
摘要
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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