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Synthesis 2014; 46(20): 2789-2793
DOI: 10.1055/s-0034-1378521
DOI: 10.1055/s-0034-1378521
paper
A Concise Synthesis of 1-Oxygenated Carbazole Alkaloids, Clausine E and Clausine F
Authors
Further Information
Publication History
Received: 06 May 2014
Accepted after revision: 25 June 2014
Publication Date:
30 July 2014 (online)
Abstract
A rapid entry into naturally occurring and biologically important 1-oxygenated carbazole clausine E was established through Wittig reaction and annulation. Further O-prenylation of clausine E by Mitsunobu reaction followed by p-Claisen rearrangement delivered clausine F.
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References
- 1 Schmidt AW, Reddy KR, Knölker H.-J. Chem. Rev. 2012; 112: 3193
- 2a Ito C, Katsuno S, Ohta H, Omura M, Kajiura I, Furukawa H. Chem. Pharm. Bull. 1997; 45: 48
- 2b Wu T.-S, Huang S.-C, Wu P.-L, Teng C.-M. Phytochemistry 1996; 43: 133
- 3 Wu T.-S, Huang S.-C. Chem. Pharm. Bull. 1992; 40: 1069
- 4 Lin W, Wang Y, Lin S, Li C, Zhou C, Wang S, Huang H, Liu P, Ye G, Shen X. Eur. J. Med. Chem. 2012; 47: 214
- 5 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
- 6 Sunthitikawinsakul A, Kongkathip N, Kongkathip B, Phonnakhu S, Daly JW, Spande TF, Nimit Y, Rochanaruangrai S. Planta Med. 2003; 69: 155
- 7 Chakraborty A, Chowdhury BK, Bhattacharyya P. Phytochemistry 1995; 40: 295
- 8 Yenjai C, Sripontan S, Sriprajun P, Kittakoop P, Jintasirikul A, Tanticharoen M, Thebtaranonth Y. Planta Med. 2000; 66: 277
- 9 Kongkathip B, Kongkathip N, Sunthitikawinsakul A, Napaswat C, Yoosook C. Phytother. Res. 2005; 19: 728
- 10 Knölker H.-J, Reddy KR. Chem. Rev. 2002; 102: 4303
- 11 Roy J, Jana AK, Mal D. Tetrahedron 2012; 68: 6099
- 12a Knölker H.-J. Chem. Lett. 2009; 38: 8
- 12b Knölker H.-J, Reddy KR. The Alkaloids . Vol. 65. Cordell GA. Academic Press; Amsterdam: 2008: 1-430 ; and references therein
- 13 Chakraborty DP, Chowdhury BK. J. Org. Chem. 1968; 33: 1265
- 14 Moody CJ. Synlett 1994; 681
- 15 Brenna E, Fuganti C, Serra S. Tetrahedron 1998; 54: 1585
- 16 Bringmann G, Tasler S, Endress H, Peters K, Peters E.-M. Synthesis 1998; 1501
- 17 Bergman J, Johnson A.-L. Org. Prep. Proced. Int. 2006; 38: 593
- 18 Tohyama S, Choshi T, Azuma S, Fujioka H, Hibino S. Heterocycles 2009; 79: 955
- 19 Alayrac C, Schollmeyer D, Witulski B. Chem. Commun. 2009; 1464
- 20 Lebold TP, Kerr MA. Org. Lett. 2008; 10: 997
- 21 Kajiyama D, Inoue K, Ishikawa Y, Nishiyama S. Tetrahedron 2010; 66: 9779
- 22 Yang W, Zhou J, Wang B, Ren H. Chem. Eur. J. 2011; 17: 13665
- 23 Nishiyama T, Choshi T, Kitano K, Hibino S. Tetrahedron Lett. 2011; 52: 3876
- 24a Jana AK, Pahari P, Mal D. Synlett 2012; 1769
- 24b Jana AK, Mal D. Chem. Commun. 2010; 46: 4411
- 24c Mal D, Senapati B, Pahari P. Tetrahedron 2007; 63: 3768
- 24d Mal D, Senapati B, Pahari P. Tetrahedron Lett. 2006; 47: 1071
- 25a Börger C, Knölker H.-J. Tetrahedron 2012; 68: 6727
- 25b Börger C, Krahl MP, Gruner M, Kataeva O, Knölker H.-J. Org. Biomol. Chem. 2012; 10: 5189
- 25c Youn SW, Bihn JH, Kim BS. Org. Lett. 2011; 13: 3738
- 25d Fuchsenberger M, Forke R, Knölker H.-J. Synlett 2011; 2056
- 25e Ackermann L, Althammer A, Mayer P. Synthesis 2009; 3493
- 25f Schmidt M, Knölker H.-J. Synlett 2009; 2421
- 25g Börger C, Knölker H.-J. Synlett 2008; 1698
- 25h Liégault B, Lee D, Huestis MP, Stuart DR, Fagnou K. J. Org. Chem. 2008; 73: 5022
- 26a Krahl MP, Kataeva O, Schmidt AW, Knölker H.-J. Eur. J. Org. Chem. 2013; 59
- 26b Gruner KK, Hopfmann T, Matsumoto K, Jäger A, Katsuki T, Knölker H.-J. Org. Biomol. Chem. 2011; 9: 2057
- 26c Thomas C, Kataeva O, Knölker H.-J. Synlett 2011; 2663
- 26d Knott KE, Auschill S, Jäger A, Knölker H.-J. Chem. Commun. 2009; 1467
- 26e Czerwonka R, Reddy KR, Baum E, Knölker H.-J. Chem. Commun. 2006; 711
- 26f Kataeva O, Krahl MP, Knölker H.-J. Org. Biomol. Chem. 2005; 3: 3099
- 26g Knölker H.-J, Fröhner W, Reddy KR. Eur. J. Org. Chem. 2003; 740
- 26h Knölker H.-J, Wolpert M. Tetrahedron 2003; 59: 5317
- 26i Knölker H.-J, Fröhner W. Tetrahedron Lett. 1997; 38: 1535
- 26j Knölker H.-J, Bauermeister M, Pannek J.-B. Chem. Ber. 1992; 125: 2783
- 26k Knölker H.-J, Bauermeister M. J. Chem. Soc., Chem. Commun. 1990; 664
- 26l Knölker H.-J, Bauermeister M. J. Chem. Soc., Chem. Commun. 1989; 1468
- 27 Sripisut T, Cheenpracha S, Ritthiwigrom T, Prawat U, Laphookhieo S. Rec. Nat. Prod. 2012; 6: 386
- 28 Thomas C, Knölker H.-J. Tetrahedron Lett. 2013; 54: 591
- 29a Parvatkar PT, Torney PS, Tilve SG. Curr. Org. Synth. 2013; 10: 288
- 29b Majik MS, Parameswaran PS, Tilve SG. J. Org. Chem. 2009; 74, 3591
- 29c Patre RE, Shet JB, Parameswaran PS, Tilve SG. Tetrahedron Lett. 2009; 50: 6488
- 30 Strandtmann MV, Cohen MP, Puchalski C, Shavel J. J. Org. Chem. 1968; 33: 4306
- 31 Cuong NM, Wilhelm H, Porzel A, Arnold N, Wessjohann L. Nat. Prod. Res. 2008; 22: 950
- 32 Nakazono M, Jinguji A, Nanbu S, Kuwano R, Zheng Z, Saita K, Oshikawa Y, Mikuni Y, Murakami T, Zhao Y, Sasaki S, Zaitsu K. Phys. Chem. Chem. Phys. 2010; 12: 9783
- 33 El-Rayyes NR. J. Prakt. Chem. 1974; 316: 386