ChemRxiv
These are preliminary reports that have not been peer-reviewed. They should not be regarded as conclusive, guide clinical practice/health-related behavior, or be reported in news media as established information. For more information, please see our FAQs.
1/1
2 files

A Practical, Component-Based Synthetic Route to Methylthiolincosamine Permitting Facile Northern-Half Diversification of Lincosamide Antibiotics

preprint
submitted on 28.03.2021, 14:04 and posted on 30.03.2021, 05:26 by Matthew Mitcheltree, Jack W. Stevenson, Amarnath Pisipati, Andrew G. Myers
The development of a flexible, component-based synthetic route to the aminosugar fragment of the lincosamide antibiotics is described. This synthetic route hinges on the application and extension of nitroaldol chemistry to forge strategic bonds within complex aminosugar targets, and employs a glycal epoxide as a versatile glycosyl donor for the installation of various anomeric groups. Through building-block exchange and late-stage functionalization, this route affords access to a host of rationally designed lincosamides otherwise inaccessible by semisynthesis, and underpins a platform for the discovery of new lincosamide antibiotics.

Funding

Graduate Research Fellowship Program (GRFP) DGE1144152

Harvard College Research Program

Blavatnik Biomedical Accelerator at Harvard University

LEO Foundation Research Grant LF18006

History

Email Address of Submitting Author

m.mitcheltree@gmail.com

Institution

Harvard University

Country

United States of America

ORCID For Submitting Author

0000-0003-3774-628X

Declaration of Conflict of Interest

A.G.M. and M.J.M. have filed an international patent application WO/2019/032956 ‘Lincosamide Antibiotics and Uses Thereof.’

Exports