RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml
Synlett 2012; 23(12): 1769-1774
DOI: 10.1055/s-0031-1290380
DOI: 10.1055/s-0031-1290380
letter
Lateral Lithiation-Initiated Annulations in the Synthesis of 1-Oxygenated Carbazole Alkaloids and a Cycloheptacarbazole
Weitere Informationen
Publikationsverlauf
Received: 31. März 2012
Accepted after revision: 23. April 2012
Publikationsdatum:
21. Juni 2012 (online)
![](https://www.thieme-connect.de/media/synlett/201212/lookinside/thumbnails/10.1055-s-0031-1290380-1.jpg)
Abstract
Anionic [4+2] annulation of lithiated furoindolones with dimethyl maleate followed by selective demethoxycarbonylation provides an efficient synthetic route to 3-methoxycarbonylcarbazoles. The route has led to the straightforward synthesis of two natural products, namely clausine E, mukonine, and their 4-prenyl analogues. A new route to cyclohepta[d,e,f]carbazole was also uncovered during the investigations.
Key words
annulation - selective demethoxycarbonylation - prenylcarbazole - cyclohepta[d,e,f]carbazoleSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
-
References and Notes
- 1a Senthilkumar N, Somannavar YS, Reddy SB, Sinha BK, Narayan GK. A. S. S, Dandala R, Mukkanti K. Synth. Commun. 2010; 41: 268
- 1b Dubois EA, van den Bos JC, Doornbos T, van Doremalen PA. P. M, Somsen GA, Vekemans JA. J. M, Janssen AG. M, Batink HD, Boer GJ. J. Med. Chem. 1996; 39: 3256
- 1c Mousset D, Rabot R, Bouyssou P, Coudert G, Gillaizeau I. Tetrahedron Lett. 2010; 51: 3987
- 1d Rajeshwaran GG, Mohanakrishnan AK. Org. Lett. 2011; 13: 1418
- 1e Hieda Y, Choshi T, Kishida S, Fujioka H, Hibino S. Tetrahedron Lett. 2010; 51: 3593
- 1f Knölker H.-J, Knöll J. Chem. Commun. 2003; 10: 1170
- 1g Knölker HJ, Reddy KR. Chem. Rev. 2002; 102: 4303
- 1h Chakraborty DP. Chemistry and Biology of Carbazole Alkaloids . In The Alkaloids . Vol. 44. Cordell GA. Academic Press; New York: 1993. 257-364 ; and references cited therein
- 1i Knölker H.-J. Curr. Org. Synth. 2004; 1: 309
- 1j Knölker H.-J. Top. Curr. Chem. 2005; 244: 115
- 2a Peciuraite V, Grigalevicius S, Simokaitiene J, Grazulevicius JV. J. Photochem. Photobiol. A 2006; 182: 38
- 2b Grigalevicius S, Tsai M.-H, Grazulevicius JV, Wu C.-C. Photochem. Photobiol. A 2005; 174: 125
- 2c Yeh K.-M, Lee C.-C, Chen Y. J. Polym. Sci., Part A: Polym. Chem. 2008; 46: 5180
- 2d Vaitkeviciene V, Kruzinauskiene A, Grigalevicius S, Grazulevicius JV, Rutkaite R, Jankauskas V. Synth. Met. 2008; 158: 383
- 2e Wang H.-Y, Liu F, Xie L.-H, Tang C, Peng B, Huang W, Wei W. J. Phys. Chem. C 2011; 115: 6961
- 2f Youn SW, Bihn JH, Kim BS. Org. Lett. 2011; 13: 3738
- 3a Maneerat W, Laphookhieo S. Heterocycles 2010; 81: 1261
- 3b Ito C, Itoigawa M, Aizawa K, Yoshida K, Ruangrungsi N, Furukawa H. J. Nat. Prod. 2009; 72: 1202
- 3c Ito C, Katsuno S, Itoigawa M, Ruangrungsi N, Mukainaka T, Okuda M, Kitagawa Y, Tokuda H, Nishino H, Furukawa H. J. Nat. Prod. 2000; 63: 125 ; and references therein
- 4a Knölker H.-J. Chem. Lett. 2009; 38: 8
- 4b Knölker H.-J, Reddy KR. The Alkaloids . Cordell GA. Academic Press; Amsterdam: 2008. Vol. 65 1-430 ; and references therein
- 4c Thomas C, Kataeva O, Knölker H.-J. Synlett 2011; 2663
- 4d Muege F, Ronny F, Knölker H.-J. Synlett 2011; 2056
- 5a Ackermann L, Althammer A, Mayer P. Synthesis 2009; 3493
- 5b Schmidt M, Knölker H.-J. Synlett 2009; 2421
- 5c Fuchsenberger M, Forke R, Knölker H.-J. Synlett 2011; 2056
- 6 Alaric C, Schollmeyer D, Witulski B. Chem. Commun. 2009; 1464
- 7a Mal D, Senapati B, Pahari P. Tetrahedron 2007; 63: 3768
- 7b Mal D, Senapati B, Pahari P. Tetrahedron Lett. 2006; 47: 1071
- 7c Jana AK, Mal D. Chem. Commun. 2010; 46: 4411
- 8 Kajiyama D, Inoue K, Ishikawa Y, Nishiyama S. Tetrahedron 2010; 66: 9779
- 9 Nishiyama T, Choshi T, Kitano K, Hibino S. Tetrahedron Lett. 2011; 52: 3876
-
10 Liger F, Popowycz F, Besson T, Picot L, Galmarini CM, Joseph B. Bioorg. Med. Chem. 2007; 15: 5615
- 11 General Procedure for the Annulation with LDA In a flame-dried flask flushed with nitrogen, LDA (9 mmol) was prepared by adding N,N-diisopropylamine (9 mmol) to a solution of n-BuLi (9 mmol, 1.6 M in hexane) in THF (20 mL) at –78 °C under nitrogen atmosphere. After the solution was stirred for 10 min at –78 °C, furoindolone (3 mmol) in THF (10 mL) was added dropwise over 5 min. The reaction mixture was stirred at the same temperature for 15 min, and a solution of the appropriate Michael acceptor (3.6 mmol) in THF (10 mL) was added dropwise. The reaction mixture was further stirred and allowed to warm slowly to r.t. over 3 h. The dark reddish brown solution was then quenched with a sat. NH4Cl solution. The resulting mixture was concentrated under reduced pressure, and the residue extracted with EtOAc (3 × 100 mL). The combined extracts were washed with brine (3 × 1/3 vol.), dried (Na2SO4), and concentrated to provide crude product which was purified by column chromatography
- 12 Brenna E, Fuganti C, Serra S. Tetrahedron 1998; 54: 1585
- 13 Kawasaki T, Kimachi T. Tetrahedron 1999; 55: 6847
- 14 Font M, Monge A, Cuartero A, Elorriaga A, Martinez-Irujo JJ, Alberdi E, Santiago E, Prieto I, Lasarte JJ. Eur. J. Med. Chem. 1995; 963
- 15 Haddach AA, Kellemanb A, Deaton-Rewolinskia MV. Tetrahedron Lett. 2002; 43: 399
- 16 Experimental Procedure for the Synthesis of Cyclohepta[d,e,f]carbazole 42 To a solution of compound 40 (20 mg, 0.05 mmol) in CH2Cl2 (8 mL) was added AlCl3 (32 mg, 0.25 mmol), and the resulting mixture was stirred at r.t. for 3 h. After the completion of the reaction, the solvent was evaporated and the residue extracted with EtOAc (2 × 40 mL). The organic extracts were washed successfully with H2O (10 mL) and brine (5 mL), dried (Na2SO4), and concentrated under reduced pressure. Column chromatography of the residue on silica gel afforded compound 42 as yellow solid. Yield 67% (10 mg); Rf = 0.3 (EtOAc–PE, 1:5); mp 165–168 °C; νmax (KBr): 2920, 1705, 1090, 804 cm–1. 1H NMR (200 MHz, CDCl3): δ = 8.56 (br s, 1 H), 7.53 (s, 1 H), 7.45–7.25 (m, 3 H), 5.82 (br s, 1 H), 3.93 (s, 3 H), 3.73–3.65 (m, 2 H), 2.20–2.12 (m, 2 H), 1.46 (s, 6 H). 13C NMR (50 MHz, CDCl3): δ = 169.2, 147.7, 139.9, 138.0, 135.5, 131.7, 126.0, 125.2, 122.0, 119.3, 117.0, 112.8, 108.5, 52.0, 39.2, 38.6, 30.8, 29.8, 29.3. HRMS: m/e calcd for C19H20NO3 [MH]+: 310.1443; found: 310.1450
- 17 Freiermuth B, Wirz J. Angew. Chem. 1988; 100: 589
- 18 Wiwel P, Hinnemann B, Hidalgo-Vivas A, Zeuthen P, Petersen BO, Duus J. Ind. Eng. Chem. Res. 2010; 49: 3184
- 19 Mitchell G, Rees CW. J. Chem. Soc., Perkin Trans. 1 1987; 403