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Synthesis 2012; 44(21): 3327-3336
DOI: 10.1055/s-0032-1317175
DOI: 10.1055/s-0032-1317175
paper
Synthetic Approach for Constructing the 1-Oxygenated Carbazole Core and Its Application to the Preparation of Natural Alkaloids
Further Information
Publication History
Received: 26 June 2012
Accepted after revision: 08 August 2012
Publication Date:
23 August 2012 (online)
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Abstract
An efficient synthetic approach for the construction of the 1-oxygenated carbazole core is described. The condensation of cyclohexane-1,2-diones with a series of anilines yielded the corresponding 2-anilinocyclohex-2-en-1-ones, followed by the one-pot aromatization/methylation process of the latter to provide N-aryl-2-methoxyanilines. A palladium(II)-catalyzed cyclization of these N-aryl-2-methoxyanilines afforded the desired 1-methoxycarbazole frame in high overall yields. This protocol was implemented for the total synthesis of the naturally occurring glycozolicine and 6-methoxymurrayanine.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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References
- 1a Pindur U. Chimia 1990; 44: 406
- 1b Knölker H.-J, Reddy KR. Chem. Rev. 2002; 102: 4303
- 1c Knölker H.-J, Reddy KR. Chemistry and Biology of Carbazole Alkaloids . In The Alkaloids Chemistry and Biology . Vol. 65. Cordell GA. Academic Press; Amsterdam: 2008
- 1d Schmidt AW, Reddy KR, Knölker H.-J. Chem. Rev. 2012; 112: 3193
- 1e Bauer I, Knölker H.-J. Top. Curr. Chem. 2012; 309: 203
- 2a Chakraborty DP. Planta Med. 1980; 39: 97
- 2b Randelia BE, Patel BP. Experientia 1982; 38: 529
- 2c Fiebig M, Pezzuto JM, Soejarto DD, Kinghorn AD. Phytochemistry 1985; 24: 3041
- 2d Chakraborty A, Chowdhury BK, Bhattacharyya P. Phytochemistry 1995; 40: 295
- 2e Chakraborty A, Saha C, Podder G, Chowdhury BK, Bhattacharyya P. Phytochemistry 1995; 38: 787
- 2f Wu T.-S, Huang S.-C, Wu P.-L, Teng C.-M. Phytochemistry 1996; 43: 133
- 2g Wu T.-S, Chan Y.-Y, Liou M.-J, Lin F.-W, Shi L.-S, Chen K.-T. Phytother. Res. 1998; 12: S80
- 2h Bringmann G, Ledermann A, Holenz J, Kao M.-T, Busse U, Wu HG, François G. Planta Med. 1998; 64: 54
-
2i Liger F, Popowycz F, Besson T, Picot L, Galmarini CM, Joseph B. Bioorg. Med. Chem. 2007; 15: 5615
- 2j Songsiang U, Thongthoom T, Boonyarat C, Yenjai C. J. Nat. Prod. 2011; 74: 208
- 3a Scott TL, Yu X, Gorugantula SP, Carrero-Martínez G, Söderberg BC. G. Tetrahedron 2006; 62: 10835
- 3b Kitawaki T, Hayashi Y, Ueno A, Chida N. Tetrahedron 2006; 62: 6792
-
3c Stokes BJ, Jovanovic B, Dong H, Richert KJ, Riell RD, Driver TG. J. Org. Chem. 2009; 74: 3225
- 4a Knölker H.-J, Bauermeister M. J. Chem. Soc., Chem. Commun. 1990; 664
- 4b Knölker H.-J, Bauermeister M. Tetrahedron 1993; 49: 11221
- 4c Knölker H.-J, Wolpert M. Tetrahedron Lett. 1997; 38: 533
- 4d Bringmann G, Tasler S, Endress H, Peters K, Peters E.-M. Synthesis 1998; 1501
- 4e Knölker H.-J, Wolpert M. Tetrahedron 2003; 59: 5317
- 4f Kuwahara A, Nakano K, Nozaki K. J. Org. Chem. 2005; 70: 413
- 4g Mal D, Senapati B, Pahari P. Tetrahedron Lett. 2006; 47: 1071
- 4h Sridharan V, Martin MA, Menéndez JC. Synlett 2006; 2375
- 4i Tohyama S, Choshi T, Azuma S, Fujioka H, Hibino S. Heterocycles 2009; 79: 955
- 4j Fuchsenberger M, Forke R, Knölker H.-J. Synlett 2006; 2056
- 4k Yang W, Zhou J, Wang B, Ren H. Chem.–Eur. J. 2011; 17: 13665
- 4l Börger C, Krahl MP, Gruner M, Kataeva O, Knölker H.-J. Org. Biomol. Chem. 2012; 10: 5189
- 5a Chakraborty DP, Chowdhury BK. J. Org. Chem. 1968; 33: 1265
- 5b Chakraborty DP, Chatterji D, Chowdhury BK. J. Indian Chem. Soc. 1971; 48: 225
- 5c Chakraborty DP, Islam A, Bhattacharyya P. J. Org. Chem. 1973; 38: 2728
- 5d Ramesh K, Kapil RS. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1986; 25: 462
- 5e Murakami Y, Yokoo H, Watanabe T. Heterocycles 1998; 49: 127
- 5f Miller CP, Bhaket P, Muthukaman N, Lyttle CR, Shomali M, Gallacher K, Slocum C, Hattersley G. Bioorg. Med. Chem. Lett. 2010; 20: 7516
- 6a Roy S, Chatterjee SK, Chakraborty DP. J. Indian Chem. Soc. 1985; 62: 673
- 6b Chakrabarty M, Nath AC, Khasnobis S, Chakrabarty M, Konda Y, Harigaya Y, Komiyama K. Phytochemistry 1997; 46: 751
- 6c Chakravarty AK, Sarkar T, Masuda K, Takey T, Doi H, Kotani E, Shiojima K. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2001; 40: 484
- 7a Roy S, Bhattacharyya L, Chakraborty DP. J. Indian Chem. Soc. 1982; 59: 1369
- 7b Bhattacharyya P, Biswas GK, Barua AK, Saha C, Roy IB, Chowdhury BK. Phytochemistry 1993; 33: 248
- 8 Mandal AB, Delgado F, Tamariz J. Synlett 1998; 87
- 9 Mandal AB, Gómez A, Trujillo G, Méndez F, Jiménez HA, Rosales MJ, Martínez R, Delgado F, Tamariz J. J. Org. Chem. 1997; 62: 4105
- 10 Bautista R, Bernal P, Montiel LE, Delgado F, Tamariz J. Synthesis 2011; 929 ; and references cited therein
- 11a Åkermark B, Eberson L, Jonsson E, Pettersson E. J. Org. Chem. 1975; 40: 1365
- 11b Knölker H.-J, O’Sullivan N. Tetrahedron 1994; 50: 10893
- 11c Forke R, Krahl MP, Krause T, Schlechtingen G, Knölker H.-J. Synlett 2007; 268
- 11d Schmidt M, Knölker H.-J. Synlett 2009; 2421
- 11e Sridharan V, Martín MA, Menéndez JC. Eur. J. Org. Chem. 2009; 4614
- 11f Liu G, Zhang A. Tetrahedron Lett. 1999; 40: 341
- 11g Liégault B, Lee D, Huestis MP, Stuart DR, Fagnou K. J. Org. Chem. 2009; 74: 5022
- 11h Watanabe T, Oishi S, Fujii N, Ohno H. J. Org. Chem. 2009; 74: 4720
- 12a Bringmann G, Ledermann A, François G. Heterocycles 1995; 40: 293
- 12b Chakraborty S, Chattopadhyay G, Saha C. J. Heterocycl. Chem. 2011; 48: 331
- 13a Knölker H.-J, Reddy KR, Wagner A. Tetrahedron Lett. 1998; 39: 8267
- 13b Hagelin H, Oslob JD, Åkermark B. Chem.–Eur. J. 1999; 5: 2413
- 13c Knölker H.-J, Fröhner W, Reddy KR. Synthesis 2002; 557
- 13d Knölker H.-J, Reddy KR. Heterocycles 2003; 60: 1049
- 14a Enamines: Synthesis, Structure, and Reactions . Cook AG. Marcel Dekker; New York: 1988. Chap. 1
- 14b Häfelinger G, Mack H.-G. Enamines: General and Theoretical Aspects . In The Chemistry of Enamines, Part 1. Rappoport Z. Wiley; Chichester: 1994. Chap. 1, 1-8
- 15a Hall RJ, Jackson AH, Oliveira-Campos AM. F, Queiroz M.-JR. P, Shannon PV. R. Heterocycles 1990; 31: 401
- 15b Hall RJ, Jackson AH, Oliveira-Campos AM. F, Shannon PV. R. J. Chem. Res., Synop. 1990; 314
- 16a Murakami Y, Yokoyama Y, Okuyama N. Tetrahedron Lett. 1983; 24: 2189
- 16b Yokoyama Y, Okuyama N, Iwadate S, Momoi T, Murakami Y. J. Chem. Soc., Perkin Trans. 1 1990; 1319
- 16c Chowdury BK, Saha C. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1994; 33: 892
- 16d Deane FM, Miller CM, Maguire AR, McCarthy FO. J. Heterocycl. Chem. 2011; 48: 814
- 17 Li W.-S, McChesney JD, El-Feraly FS. Phytochemistry 1991; 30: 343
- 18a Bernal P, Benavides A, Bautista R, Tamariz J. Synthesis 2007; 1943
- 18b Börger C, Knölker H.-J. Synlett 2008; 1698
- 18c Börger C, Knölker H.-J. Tetrahedron 2012; 68: 6727
- 19 Polozov GI, Tishchenko IG. Vestn. Belorus. Un-ta., Ser. 2 1986; 1: 67
- 20 Sen AB, Grupta AK. S. J. Indian Chem. Soc. 1957; 34: 413
- 21 Coutts IG. C, Hamblin M. J. Chem. Soc., Perkin Trans. 1 1975; 2445
- 22 Barton DH. R, Donnelly DM. X, Finet J.-P, Guiry PJ. J. Chem. Soc., Perkin Trans. 1 1991; 2095
- 23 Reddy ChV, Kingston JV, Verkade JG. J. Org. Chem. 2008; 73: 3047
- 24 Shah GD, Patel BP. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1979; 18: 451
- 25 Bedford RB, Betham M. J. Org. Chem. 2006; 71: 9403
For recent examples:
For examples of synthesis of 1-oxygenated carbazoles, see:
The Pd(II)-catalyzed conversion of diarylamines into carbazoles has been a successful procedure since the pioneer work of Åkermark,11a as well as the modified and improved procedures developed more recently by Knölker et al.,11b–d Menéndez et al.,11e and other groups:11f–h