Diastereoselective Michael-Claisen Cyclizations of γ-Oxa-α,β-unsaturated Ketones en Route to 5-Oxatetracyclines

Fan Liu; Peter M Wright; Andrew G Myers

doi:10.1021/acs.orglett.6b03491

Diastereoselective Michael-Claisen Cyclizations of γ-Oxa-α,β-unsaturated Ketones en Route to 5-Oxatetracyclines

Org Lett. 2017 Jan 6;19(1):206-209. doi: 10.1021/acs.orglett.6b03491. Epub 2016 Dec 20.

Authors

Fan Liu¹, Peter M Wright¹, Andrew G Myers¹

Affiliation

¹ Department of Chemistry and Chemical Biology, Harvard University , Cambridge, Massachusetts 02138, United States.

PMID: 27996275
DOI: 10.1021/acs.orglett.6b03491

Abstract

5-Oxatetracyclines were synthesized from d-arabinose using sequential Michael-Claisen cyclization reactions via a 5-oxa-AB enone substrate. The 5-oxatetracyclines were found to have poor stability in aqueous buffer (pH 7.4, 37 °C) and showed little to no inhibition of bacterial growth (S. aureus, E. coli).

Publication types

Research Support, Non-U.S. Gov't