References and Notes
1 Part 81: Krahl MP.
Jäger A.
Krause T.
Knölker H.-J.
Org. Biomol. Chem.
2006,
4:
3215
2a
Chakraborty DP.
Roy S. In Progress in the Chemistry of Organic Natural Products
Vol. 57:
Herz W.
Grisebach H.
Kirby GW.
Steglich W.
Tamm C.
Springer;
Wien:
1991.
p.71
2b
Chakraborty DP. In The Alkaloids
Vol. 44:
Cordell GA.
Academic Press;
New York:
1993.
p.257
3a
Knölker H.-J.
Reddy KR.
Chem. Rev.
2002,
102:
4303
3b
Knölker H.-J.
Top. Curr. Chem.
2005,
244:
115
4a
Pindur U.
Chimia
1990,
44:
406
4b
Bergman J.
Pelcman B.
Pure Appl. Chem.
1990,
62:
1967
4c
Kawasaki T.
Sakamoto M.
J. Indian Chem. Soc.
1994,
71:
443
4d
Moody CJ.
Synlett
1994,
681
4e
Hibino S.
Sugino E. In Advances in Nitrogen Heterocycles
Vol. 1:
Moody CJ.
JAI Press;
Greenwich (CT):
1995.
p.205
4f
Kirsch GH.
Curr. Org. Chem.
2001,
5:
507
4g
Lemster T.
Pindur U.
Recent Res. Dev. Org. Bioorg. Chem.
2002,
5:
99
5
Kataeva O.
Krahl MP.
Knölker H.-J.
Org. Biomol. Chem.
2005,
3:
3099
6a
Chakraborty DP.
Das K.
Das BP.
Chowdhury BK.
Trans. Bose Res. Inst.
1975,
38:
1
6b
Chowdhury DN.
Basak SK.
Das BP.
Curr. Sci.
1978,
47:
490
7a
Chakraborty DP.
Tetrahedron Lett.
1966,
661
7b
Chakraborty DP.
Phytochemistry
1969,
8:
769
8a
Adesina SK.
Olatunji OA.
Bergenthal D.
Reisch J.
Pharmazie
1988,
43:
221
8b
Ito C.
Thoyama Y.
Omura M.
Kajiura I.
Furukawa H.
Chem. Pharm. Bull.
1993,
41:
2096
9
Chakravarty AK.
Sarkar T.
Masuda K.
Shiojima K.
Phytochemistry
1999,
50:
1263
10
Rastogi K.
Kapil RS.
Popli SP.
Phytochemistry
1980,
19:
945
11
Li W.-S.
McChesney JD.
El-Feraly FS.
Phytochemistry
1991,
30:
343
12
Adesina SK.
Olugbade TA.
Akinwusi DD.
Bergenthal D.
Pharmazie
1997,
52:
720
13a
Mukherjee S.
Mukherjee M.
Ganguly SN.
Phytochemistry
1983,
22:
1064
13b
Bhattacharyya P.
Sarkar T.
Chakraborty A.
Chowdhury BK.
Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.
1984,
23:
49
14
Wu S.-L.
Li W.-S.
Chin. Pharm. J.
1999,
51:
227
15
Kumar V.
Reisch J.
Wickramasinghe A.
Aust. J. Chem.
1989,
42:
1375
16
Ma C.
Case RJ.
Wang Y.
Zhang H.-J.
Tan GT.
Hung NV.
Cuong NM.
Franzblau SG.
Soejarto DD.
Fong HHS.
Pauli GF.
Planta Med.
2005,
71:
261
17
Ito C.
Furukawa H.
Chem. Pharm. Bull.
1990,
38:
1548
18a
Chakraborty DP.
Das KC.
Chowdhury BK.
Sci. Cult.
1966,
32:
245
18b
Chakraborty DP.
Das KC.
Chowdhury BK.
Chem. Ind.
1966,
1684
18c
Carruthers W.
J. Chem. Soc., Chem. Commun.
1966,
272
18d
Bhattacharyya P.
Mitra AR.
Chakraborty DP.
J. Indian Chem. Soc.
1976,
53:
321
18e
Bhattacharyya P.
Jash SS.
Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.
1986,
25:
1056
18f
Kudav DP.
Kulkarni NN.
Hosangadi BD.
J. Chem. Res., Synop.
1994,
266
19a
Anwer F.
Masaldan AS.
Kapil RS.
Popli SP.
Indian J. Chem.
1973,
11:
1314
19b
Chowdhury BK.
Saha C.
Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.
1994,
33:
892
20
Iwao M.
Takehara H.
Furukawa S.
Watanabe M.
Heterocycles
1993,
36:
1483
21a
Fröhner W.
Krahl MP.
Reddy KR.
Knölker H.-J.
Heterocycles
2004,
63:
2393
21b
Knölker H.-J.
Reddy KR. In Selected Methods for Synthesis and Modification of Heterocycles - The Chemistry and Biological Activity of Natural Indole Systems
Part 1, Vol. 4:
Kartsev VG.
ICSPF Press;
Moscow:
2005.
p.166
22a
Hartwig JF.
Angew. Chem. Int. Ed.
1998,
37:
2046
22b
Muci AR.
Buchwald SL.
Top. Curr. Chem.
2002,
219:
131
23a
Åkermark B.
Eberson L.
Jonsson E.
Petersson E.
J. Org. Chem.
1975,
40:
1365
23b
Miller RB.
Moock T.
Tetrahedron Lett.
1980,
21:
3319
23c
Furukawa H.
Ito C.
Yogo M.
Wu T.-S.
Chem. Pharm. Bull.
1986,
34:
2672
23d
Knölker H.-J.
O’Sullivan N.
Tetrahedron
1994,
50:
10893
23e
Knölker H.-J.
Fröhner W.
Reddy KR.
Synthesis
2002,
557
23f
Knölker H.-J.
Reddy KR.
Heterocycles
2003,
60:
1049
23g
Knölker H.-J.
Knöll J.
Chem. Commun.
2003,
1170
24 The preparation of compound 10 using a Pd(0)-catalyzed amination has been reported previously, albeit in lower yield (77%): Urgaonkar S.
Xu J.-H.
Verkade JG.
J. Org. Chem.
2003,
68:
8416
25
Corey EJ.
Gilman NW.
Ganem BE.
J. Am. Chem. Soc.
1968,
90:
5616
26a
Wilke G.
Bogdanovic B.
Hardt P.
Heimbach P.
Keim W.
Kröner M.
Oberkirch W.
Tanaka K.
Steinrücke E.
Walter D.
Zimmermann H.
Angew. Chem., Int. Ed. Engl.
1966,
5:
151
26b
Corey EJ.
Semmelhack MF.
J. Am. Chem. Soc.
1967,
89:
2755
26c
Plieninger H.
Sirowej H.
Chem. Ber.
1971,
104:
2027
26d
Inoue S.
Yamaguchi R.
Saito K.
Sato K.
Bull. Chem. Soc. Jpn.
1974,
47:
3098
26e
Billington DC.
Chem. Soc. Rev.
1985,
14:
93
27 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): ν = 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-d
6): 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-d
6): δ = 18.34 (CH3), 21.67 (CH3), 25.83 (CH3), 26.24 (CH2), 109.21 (CH), 111.09 (CH), 115.52 (CH), 122.15 (C), 122.97 (C), 123.29 (CH), 124.05 (CH), 124.34 (C), 126.87 (CH), 127.59 (C), 131.86 (C), 136.06 (C), 140.13 (C), 148.19 (C). MS (100 °C): m/z (%) = 265 (100) [M+], 210 (71), 209 (87), 181 (14), 180 (19), 167 (9). HRMS: m/z calcd for C18H19NO [M+]: 265.1467; found: 265.1454.
28 Crystal data for the bromocarbazole 12: C14H10BrNO2, 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, D
c = 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 (R
int = 0.0629), 168 parameters. The structure was solved by direct methods and refined by full-matrix least-squares on F
2; final R indices [I > 2σ(I)]: R
1 = 0.0405, wR
2 = 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 Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
29 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): ν = 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-d
6): 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 (br s, 1 H). 13C NMR and DEPT (125 MHz, acetone-d
6): δ = 18.43 (CH3), 25.80 (CH3), 26.19 (CH2), 110.07 (CH), 111.79 (CH), 116.63 (CH), 122.76 (C), 123.26 (C and CH), 124.05 (C), 126.63 (CH), 127.40 (CH), 129.39 (C), 132.83 (C), 136.07 (C), 145.38 (C), 149.40 (C), 191.85 (CHO). MS (150 °C): m/z (%) = 279 (93) [M+], 224 (81), 223 (100), 208 (7), 195 (13), 194 (10), 183 (11), 167 (11). HRMS: m/z calcd for C18H17NO2 [M+]: 279.1259; found: 279.1262. Anal. Calcd (%) for C18H17NO2: C, 77.40; H, 6.13; N, 5.01. Found: C, 77.50; H, 6.22; N, 5.03.
30
Röhrkasten R.
Konrad M. In Methoden der Organischen Chemie (Houben-Weyl)
Vol. E6b:
Kreher RP.
Thieme;
Stuttgart:
1994.
p.94
31 Amberlyst 15 from Fluka (art. 06423).
32 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): ν = 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), 120.42 (C), 120.93 (CH), 123.23 (C), 126.54 (CH), 128.71 (C), 135.92 (C), 137.65 (C), 145.14 (CH), 150.27 (C). MS (20 °C): m/z (%) = 221 (100) [M+], 220 (53), 192 (7), 191 (8). HRMS: m/z calcd for C15H11NO [M+]: 221.0841; found: 221.0853. Anal. Calcd (%) for C15H11NO: C, 81.43; H, 5.01; N, 6.33. Found: C, 81.23; H, 5.07; N, 6.24.
Isoeustifoline-D (15): colorless crystals; mp 154 °C. UV (MeOH): λmax = 247, 255, 264, 272 (sh), 304, 311 (sh), 316, 349, 365 nm. IR (ATR): ν = 3403, 2918, 2854, 1617, 1533, 1504, 1483, 1446, 1342, 1326, 1307, 1292, 1262, 1220, 1175, 1154, 1125, 1097, 1030, 978, 879, 840, 799, 790, 756, 731, 697, 619 cm-1. 1H NMR (500 MHz, CDCl3): δ = 2.54 (s, 3 H), 6.83 (d, J = 2.1 Hz, 1 H), 7.24 (d, J = 8.2 Hz, 1 H), 7.28 (d, J = 8.2 Hz, 1 H), 7.47 (s, 1 H), 7.68 (d, J = 2.1 Hz, 1 H), 7.81 (br s, 1 H), 7.89 (s, 1 H), 8.10 (s, 1 H). 13C NMR and DEPT (125 MHz, CDCl3): δ = 21.39 (CH3), 100.56 (CH), 101.66 (CH), 106.53 (CH), 110.05 (CH), 120.17 (CH), 121.93 (C), 123.65 (C), 126.73 (C), 127.23 (CH), 128.34 (C), 137.38 (C), 139.00 (C), 145.65 (CH), 150.38 (C). MS (20 °C): m/z (%) = 221 (100) [M+], 220 (53), 192 (7), 191 (6). HRMS: m/z calcd for C15H11NO [M+]: 221.0841; found: 221.0851. Anal. Calcd (%) for C15H11NO: C, 81.43; H, 5.01; N, 6.33. Found: C, 80.59; H, 5.06; N, 6.15.
33 Braxmeier T, Friedrichson T, Fröhner W, Jennings G, Schlechtingen G, Schroeder C, Knölker H.-J, Simons K, Zerial M, and Kurzchalia T. inventors; PCT Int. Appl. WO 2006002908.
34
Choi T.
Czerwonka R.
Fröhner W.
Krahl MP.
Reddy KR.
Franzblau SG.
Knölker H.-J.
ChemMedChem
2006,
1:
812