SCOPUS 정보 검색 플랫폼

Volumn , Issue 6, 2007, Pages 954-958

Convergent synthesis of the central heterocyclic domain of micrococcin P1

Author keywords

Bohlmann Rahtz; Micrococcin; Pyridines; Thiazoles; Thiopeptide antibiotics

Indexed keywords

ANTIBIOTIC AGENT; ENAMINE; HETEROCYCLIC COMPOUND; MICROCOCCIN P1; THIOSTREPTON; UNCLASSIFIED DRUG;

ARTICLE; COLUMN CHROMATOGRAPHY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; NUCLEAR MAGNETIC RESONANCE;

EID: 34247130450 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-973870 Document Type: Article

Times cited : (33)

References (22)

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19
- 34247123012
- tert-Butyl 4-{4-[2-(ethoxycarbonyl)-1-aminovinyl]thiazol-2- yl}-2,2,5-trimethyloxazolidine-3-carboxylate(4) β-Ketoester 8 (100 mg, 0.24 mmol) was dissolved in toluene-AcOH (5:1, 3 mL) and NH 4OAc (2.24 g, 29.09 mmol, 120 equiv) was added. The mixture was irradiated in a sealed tube at 150°C with continuous cooling for 10 min using a CEM Discover® single-mode microwave synthesiser (initial power 300 W, The mixture was cooled to r.t, evaporated in vacuo and partitioned between H2O (20 mL) and EtOAc (10 mL, The aqueous layer was further extracted with EtOAc (2 x 10 mL) and the combined organic extracts were washed sequentially with sat. aq NaHCO3 (15 mL) and brine (15 mL, dried (Na2SO4) and evaporated in vacuo. Purification by column chromatography on silica, eluting with PE-EtOAc (3:1) gave the title compound 412 as a viscous yellow oil. Methyl 2-(propynoyl)thiazole- 4-carb
- 14 as a yellow solid.

20
- 34247156883
- tert-Butyl 4-{4-[2-(ethoxycarbonyl)-1-aminovinyl]thiazol-2- yl}-2,2,5-trimethyloxazolidine-3-carboxylate (4) Rf0.34 (PE-EtOAc, 3:1, HRMS: m/z [MH, calcd for C 19H30N3O5S: 412.1901; found: 412.1899. IR (film, 3488, 3407, 3146, 2975, 1694, 1478, 1368, 1258, 1217, 1167, 1132, 1087 cm-1. 1NMR (400 MHz, CDCl3, δ, 7.54 (br s, 1 H, thz, 6.60-7.10 (br s, 1 H, NH, 5.12 (br s, 1 H, Thr-α, 4.68 (br s, 0.4 H, Thr-β, 4.57 (br d, J, 6.2 Hz, 0.6 H, Thr-β, 4.14 (s, 1 H, C, CH, 4.12 (q, J, 7.0 Hz, 2 H, OCH2CH3, 1.64 (br s, 7 H, 1.40 (br s, 3 H, 1.34 (br d, J, 6.2 Hz, 3 H, Thr-Me, 1.24 (t, J, 7.0 Hz, 3 H, OCH2CH3, 1.10 (br s, 6 H, 13C NMR (125 MHz, CDCl3, δ, 171.9 (C, 170.4 (C, 151.8 (C, 151.2 (C, 150.6 C, 124.9
- +], 356 (17), 312 (30), 241 (30), 227 (23), 183 (15), 134 (100).

21
- 34247132430
- Methyl 2-(propynoyl)thiazole-4-carboxylate (5) mp 152°C (dec, CHCl3, Rf0.47 (PE-EtOAc, 1:1, HRMS: m/z [MH, calcd for C8H6NO3S: 196.0068; found: 196.0059. IR (CH2Cl2, 3209, 3128, 2360, 1742, 1641, 1480, 1461, 1427, 1341, 1265, 1240, 1109, 993, 960, 911, 827 cm -1. 1H NMR (250 MHz, CDCl3, δ, 8.46 (s, 1 H, 5-H, 3.93 (s, 3 H, CO2Me, 3.66 (s, 1 H, 3′-H, 13C NMR (125 MHz, CDCl3, δ, 169.01 (C, 166.16 (C, 161.06 (C, 149.18 (C, 133.81 (CH, 84.93 (CH, 78.94 (C, 52.84 (CH 3, MS (ES, m/z, 196 (100, M, H, 156 (15, 1353
- +], 156 (15), 135(3).

22
- 34247142621
- MPI domain (3) Rf0.69 (5% MeOH in CHCl 3, HRMS: m/z [MH, calcd for C34H 37N6O7S4: 769.1601; found: 769.1604. IR (CH2Cl2, 3438, 2966, 2915, 1734, 1700, 1579, 1464, 1438, 1363, 1298, 1258, 1091, 1022 cm-1. 1H NMR (400 MHz, CDCl3, δ, 8.25 (s, 1 H, thz, 8.24 (app. br s, 1 H, py-4, 8.20 (s, 1 H, thz, 8.17 (s, 1 H, thz, 7.95 (app. br s, 1 H, py-5, 6.91 (s, 1 H, thz, 4.95 (s, 0.6 H, Thr-α, 4.83 (d, J, 11.0 Hz, 0.4 H, Thr-α, 4.39 (q, J, 7.0 Hz, 2 H, OCH2CH 3, 4.36 (q, J, 7.0 Hz, 2 H, OCH2CH 3, 4.35 (br s, 1 H, Thr-β, 1.61 (br s, 3 H, 1.51 (br s, 6 H, 1.45 (br s, 3 H, 1.38 (t, J, 7.0 Hz, 3 H, OCH2C H3, 1.31 t, J, 7.0 Hz, 3 H, OCH2CH3, 1
- +], 656 (8), 639 (8), 224 (8), 141 (8).

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