Practical Synthesis of p- and o-Amino- and Methoxyphenolic Anthraquinones
Corresponding Author
Prof. Dr. K. C. Nicolaou
Department of Chemistry, BioScience Research Collaborative, Rice University, 6100 Main Street, Houston, TX 77005 (USA)
Department of Chemistry, BioScience Research Collaborative, Rice University, 6100 Main Street, Houston, TX 77005 (USA)Search for more papers by this authorDr. Min Lu
Department of Chemistry, BioScience Research Collaborative, Rice University, 6100 Main Street, Houston, TX 77005 (USA)
Search for more papers by this authorPengxi Chen
Department of Chemistry, BioScience Research Collaborative, Rice University, 6100 Main Street, Houston, TX 77005 (USA)
Search for more papers by this authorDr. Akshay A. Shah
Department of Chemistry, BioScience Research Collaborative, Rice University, 6100 Main Street, Houston, TX 77005 (USA)
Search for more papers by this authorCorresponding Author
Prof. Dr. K. C. Nicolaou
Department of Chemistry, BioScience Research Collaborative, Rice University, 6100 Main Street, Houston, TX 77005 (USA)
Department of Chemistry, BioScience Research Collaborative, Rice University, 6100 Main Street, Houston, TX 77005 (USA)Search for more papers by this authorDr. Min Lu
Department of Chemistry, BioScience Research Collaborative, Rice University, 6100 Main Street, Houston, TX 77005 (USA)
Search for more papers by this authorPengxi Chen
Department of Chemistry, BioScience Research Collaborative, Rice University, 6100 Main Street, Houston, TX 77005 (USA)
Search for more papers by this authorDr. Akshay A. Shah
Department of Chemistry, BioScience Research Collaborative, Rice University, 6100 Main Street, Houston, TX 77005 (USA)
Search for more papers by this authorAbstract
New versatile and selective methods for the syntheses of substituted amino- and methoxyphenolic anthraquinones (I–IV) based on fusion of cyanophthalides (V) and semiquinone aminals (VI, VII) under basic conditions are described.
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References
- 1Review: K. C. Nicolaou, W. M. Dai, Angew. Chem. Int. Ed. Engl. 1991, 30, 1387–1416; Angew. Chem. 1991, 103, 1453–1481.
- 2Review: K. C. Nicolaou, A. L. Smith, E. W. Yue, A. Montero, Proc. Natl. Acad. Sci. USA 1993, 90, 5881–5888.
- 3Isolation: J. Davies, H. Wang, T. Taylor, K. Warabi, X.-H. Huang, R. J. Andersen, Org. Lett. 2005, 7, 5233–5236.
- 4Total synthesis: K. C. Nicolaou, H. Zhang, J. S. Chen, J. J. Crawford, L. Pasunoori, Angew. Chem. Int. Ed. 2007, 46, 4704–4707; Angew. Chem. 2007, 119, 4788–4791.
- 5Review: K. C. Nicolaou, J. S. Chen, H. Zhang, A. Montero, Angew. Chem. Int. Ed. 2008, 47, 185–189; Angew. Chem. 2008, 120, 191–195.
- 6Patents:
- 6aN. S. Chowdari, S. Gangwar, B. Sufi, US8709431 B2, April 29, 2014;
- 6bK. C. Nicolaou, M. Lu, D. Mandal, S. Gangwar, N. S. Chowdari, Y. B. Poudel, WO2015023879 A1, February 19, 2015.
- 7Review: P. M. Wright, I. B. Seiple, A. G. Myers, Angew. Chem. Int. Ed. 2014, 53, 8840–8869; Angew. Chem. 2014, 126, 8984–9014.
- 8Isolation: C. J. Zheng, H. E. Yu, E. H. Kim, W. G. Kim, J. Antibiot. 2008, 61, 633–637.
- 9Total synthesis: K. C. Nicolaou, C. Nilewski, C. R. H. Hale, H. A. Ioannidou, A. ElMarrouni, L. G. Koch, Angew. Chem. Int. Ed. 2013, 52, 8736–8741; Angew. Chem. 2013, 125, 8898–8904.
- 10Total synthesis: K. C. Nicolaou, C. R. H. Hale, C. Nilewski, H. A. Ioannidou, A. ElMarrouni, L. G. Nilewski, K. Beabout, T. T. Wang, Y. Shamoo, J. Am. Chem. Soc. 2014, 136, 12137–12160.
- 11Isolation: F. Tomita, T. Tamaoki, J. Antibiot. 1981, 34, 1519–1524.
- 12Total synthesis: J. Švenda, N. Hill, A. G. Myers, Proc. Natl. Acad. Sci. USA 2011, 108, 6709–6714.
- 13Total synthesis: T. Magauer, D. J. Smaltz, A. G. Myers, Nat. Chem. 2013, 5, 886–893.
- 14Total synthesis: K. C. Nicolaou, Q. Cai, B. Qin, M. T. Petersen, R. J. T. Mikkelsen, P. Heretsch, Angew. Chem. Int. Ed. 2015, 54, 3074–3078; Angew. Chem. 2015, 127, 3117–3121.
- 15Unpublished results, this laboratory.
- 16J. S. Swenton, B. R. Bonke, W. M. Clark, C. P. Chen, K. V. Martin, J. Org. Chem. 1990, 55, 2027–2034.
- 17A. G. Myers, N. J. Tom, M. E. Fraley, S. B. Cohen, D. J. A. Madar, J. Am. Chem. Soc. 1997, 119, 6072–6094.
- 18M. D. Shair, T. Y. Yoon, K. K. Mosny, T. C. Chou, S. J. Danishefsky, J. Am. Chem. Soc. 1996, 118, 9509–9525.
- 19F. M. Hauser, R. P. Rhee, J. Org. Chem. 1978, 43, 178–180.
- 20G. A. Kraus, H. Sugimoto, Tetrahedron Lett. 1978, 19, 2263–2266.
10.1016/S0040-4039(01)91508-4 Google Scholar
- 21D. Mal, P. Pahari, Chem. Rev. 2007, 107, 1892–1918.
- 22S. K. Chittimalla, H. Y. Shiao, C.-C. Liao, Org. Biomol. Chem. 2006, 4, 2267–2277.
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