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. 2014 Jan 17;12(1):317–351. doi: 10.3390/md12010317

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© 2014 by the authors; licensee MDPI, Basel, Switzerland.

This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).

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Scheme 5 — Kelly’s synthesis of dimethyl sulfomycinamate. Reagents and conditions: (a) Br₂, pyridine, rt, 77%; (b) MeI, K₂CO₃, acetone, reflux, overnight 88%; (c) KMnO₄, 90 °C, 3 h; (d) ClCO₂Me, Et₃N, DMAP, CH₂Cl₂, 0 °C to rt, 2 h, 65%; (e) AlCl₃, CH₂Cl₂, reflux, 2 days, 93%; (f) Tf₂O, 2,6-lutidine, CH₂Cl₂, 0 °C, 5 min, 95%; (g) 5, PdCl₂(PPh₃)₂, 1,4-dioxane, 100 °C, overnight 97%; (h) NBS, THF, H₂O, rt, 10 min, 95%; (i) 6, THF sealed tube, 100 °C, 3 days, 65%; (j) OsO₄, NaIO₄, 1,4-dioxane, H₂O, rt 3 h, 85%; (k) 7, Sn₂Bu₆, PdCl₂(PPh₃)₂, Pd(PPh₃)₄, LiCl, 1,4-dioxane, 100 °C, overnight, 35%.