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Volumn , Issue 2, 2007, Pages 268-272

Transition metals in organic synthesis, part 82.1 First total synthesis of methyl 6-methoxycarbazole-3-carboxylate, glycomaurrol, the anti-TB active micromeline, and the furo[2,3-c]carbazole alkaloid eustifoline-D

(5) Forke, Ronny a Krahl, Micha P a Krause, Tilo a Schlechtingen, Georg a,b Knölker, Hans Joachim a,b

a DRESDEN UNIVERSITY OF TECHNOLOGY (Germany)

b JADO Technologies GmbH (Germany)

Author keywords

Alkaloids; Antibiotics; Catalysis; Nickel; Palladium

Indexed keywords

ALKALOID DERIVATIVE; CARBAZOLE DERIVATIVE; EUSTIFOLINE D; GLYCOMAURROL; GLYCOZOLININE; METHYL 6 METHOXYCARBAZOLE 3 CARBOXYLIC ACID; MICROMELINE; PALLADIUM; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; SYNTHESIS;

EID: 33847015242 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-967984 Document Type: Article

Times cited : (96)

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57
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- Pure glycomaurrol (5) was obtained by preparative HPLC on a Vydac C8 50 mm column (gradient elution with 50 mL/min MeCN-H2O, 30-60% MeCN in 30 min, Glycomaurrol (5, colorless crystals; mp 141°C. UV (MeOH, λmax, 257, 269, 292 (sh, 301, 350, 362 (sh) nm. IR (ATR, v, 3409, 3214, 2917, 1589, 1512, 1499, 1476, 1442, 1390, 1349, 1309, 1282, 1267, 1225, 1166, 1148, 1100, 1069, 1030, 954, 871, 850, 797, 739, 694, 648 cm-1. 1H NMR (500 MHz, acetone-d6, δ, 1.72 (d, J, 1.2 Hz, 3 H, 1.98 (s, 3 H, 2.51 (s, 3 H, 4.01 (d, J, 6.5 Hz, 2 H, 5.37 (t, J, 6.5 Hz, 1 H, 7.03 (d, J, 8.5 Hz, 1 H, 7.19 (d, J, 8.5 Hz, 1 H, 7.20 (m, 1 H, 7.37 (d, J, 8.2 Hz, 1 H, 7.70 (s, 1 H, 7.95 (s, 1 H, 9.94 (br s, 1 H, 13C NMR and DEPT (125 MHz, acetone-d6, δ, 18.34 (CH3, 21.67 (CH3, 25.83 CH3
- +]: 265.1467; found: 265.1454.

58
- 33847050137
- Crystal data for the bromocarbazole 12: C14H 10BrNO2, M, 304.14, monoclinic, space group: P21/c, a, 19.570(4, b, 8.296(2, c, 7.360(2) Å, β= 94.77(3)°, V, 1190.8(5) Å3, Z, 4, Dc, 1.696 g cm -3, μ, 3.444 mm-1, T, 198(2) K, λ, 0.71073 Å, θ range: 3.13-30.00°, 29544 reflections collected, 3454 independent (Rint, 0.0629, 168 parameters. The structure was solved by direct methods and refined by full-matrix least-squares on F2; final R indices [I > 2σI, R1, 0.0405, wR2, 0.0761; maximal residual electron density: 0.598 e Å-3. CCDC-628163 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallo
- -3. CCDC-628163 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/ data_request/cif.

59
- 33847031645
- Pure micromeline (6) was obtained by preparative HPLC on a Vydac C8 50 mm column (gradient elution with 50 mL/min MeCN-H2O, 30-60% MeCN in 30 min, Micromeline (6, colorless crystals; mp 205-206°C. UV (MeOH, λmax, 231, 252, 276 (sh, 278, 281, 295 (sh, 300, 340 nm. IR (ATR, v, 3156, 2963, 2911, 2854, 2740, 1663, 1649, 1629, 1603, 1566, 1522, 1464, 1446, 1371, 1310, 1291, 1271, 1228, 1202, 1181, 1164, 1120, 1063, 1028, 958, 899, 883, 851, 811, 792, 717, 663 cm-1. 1H NMR (500 MHz, acetone-d6, δ, 1.72 (d, J, 1.1 Hz, 3 H, 2.03 (s, 3 H, 4.07 (d, J, 6.4 Hz, 2 H, 5.36 (t, J, 6.4 Hz, 1 H, 7.15 (d, J, 8.5 Hz, 1 H, 7.33 (d, J, 8.5 Hz, 1 H, 7.63 (d, J, 8.5 Hz, 1 H, 7.95 (dd, J, 8.5, 1.4 Hz, 1 H, 8.03 (br s, 1 H, 8.69 (s, 1 H, 10.09 (s, 1 H, 10.70
- 2: C, 77.40; H, 6.13; N, 5.01. Found: C, 77.50; H, 6.22; N, 5.03.

60
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61
- 33847029848
- Amberlyst 15 from Fluka (art. 06423).
- Amberlyst 15 from Fluka (art. 06423).

62
- 33847045082
- A separation of the two isomers 7 and 15 was achieved by preparative HPLC on a Vydac C8 30 mm column (gradient elution with 40 mL/min MeCN-H2O, 30-46% MeCN in 32 min, Eustifoline-D (7, colorless crystals; mp 156°C. UV (MeOH, λmax, 253, 260 (sh, 268, 298, 310, 339, 354 nm. IR (ATR, v, 3406, 2919, 2856, 1615, 1575, 1484, 1443, 1432, 1409, 1360, 1300, 1275, 1242, 1229, 1209, 1139, 1074, 1051, 946, 886, 875, 800, 789, 780, 750, 731, 690, 659 cm-1. 1H NMR (500 MHz, CDCl3, δ, 2.59 (s, 3 H, 7.26 (dd, J, 8.3, 1.2 Hz, 1 H, 7.31 (d, J, 8.8 Hz, 1 H, 7.33 (dd, J, 2.0, 0.4 Hz, 1 H, 7.36 (d, J, 8.3 Hz, 1 H, 7.58 (d, J, 8.8 Hz, 1 H, 7.81 (d, J, 2.0 Hz, 1 H, 7.98 (s, 1 H, 8.03 (br s, 1 H, 13C NMR and DEPT (125 MHz, CDCl3, δ, 21.51 (CH3, 105.40 (CH, 107.38 (CH, 109.43 (CH, 110.43 (CH, 114.80 C, 120
- 11NO: C, 81.43; H, 5.01; N, 6.33. Found: C, 80.59; H, 5.06; N, 6.15.

63
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