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Asymmetric Total Synthesis of C9’-epi-Sinefungin

preprint
submitted on 17.05.2020, 20:19 and posted on 19.05.2020, 04:36 by Ludovic Decultot, Rocco L. Policarpo, Brandon Wright, Danny Huang, Matthew Shair
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 highlighted, opening an avenue for the discovery of new MTs inhibitors.

Funding

DGE1144152

History

Email Address of Submitting Author

ludovic.decultot@gmail.com

Institution

Harvard University Department of Chemistry and Chemical Biology

Country

United States of America

ORCID For Submitting Author

0000-0002-2607-2016

Declaration of Conflict of Interest

The authors declare no conflicts of interest.

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