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. Author manuscript; available in PMC: 2014 Mar 20.
Published in final edited form as: Bioconjug Chem. 2013 Feb 14;24(3):473–486. doi: 10.1021/bc300610f

Scheme 3. Syntheses of hydroxamate sideromycins (1b–3b and 1c–3c).a.

Scheme 3

aReagents and conditions: (a) 8, iPr2EtN, DMAP, CH2Cl2; 18 h, 73% for 11; 16 h, 66% for 13; 20 h, 87% for 15. (b) 10% Pd-C, H2 (1 atm), HCl (3 equiv), DMF:H2O (95:5); 41 h, 38% for 1b; 24 h, 42% for 2b; 24 h, 42% for 3b. (c) 10, iPr2EtN, DMAP, CH2Cl2; 5 h, 92% for 12; 23 h, 66% for 14; 4.5 h, 84% for 16. (d) 10% Pd-C, H2 (1 atm), MeOH; 12 h, 70% for 1c; 16 h, 86% for 2c; 16 h, 97% for 3c.