American Chemical Society
ol6b03491_si_001.pdf (9.32 MB)

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

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journal contribution
posted on 2016-12-20, 15:05 authored by Fan Liu, Peter M. Wright, Andrew G. Myers
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).