A concise asymmetric synthesis of (-)-hongconin and (-)-1-epi-hongconin

European Journal of Organic Chemistry

Volumn , Issue 22, 2010, Pages 4306-4311

  Fernandes, Rodney A ^a   Chavan, Vijay P ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

Author keywords

Annulation; Asymmetric synthesis; Cyclization; Natural products; Quinones

Indexed keywords

EID: 77954964826     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201000560     Document Type: Article

References (30)

1. Z. Chen, H. Huang, C. Wang, Y. Li, J. Ding, S. Ushio, N. Hiroshi, I. Yoichi, Chem. Pharm, Bull. 1986, 34, 2743-2746.
2. Z. Chen, H. Huang, C. Wang, Y. Li, J. Ding, Chin, Tradit. Herb. Drugs 1981, 12, 483-484 (in Chinese).
3. J. Ding, H. Huang, Zhongcaoyao 1982, 13, 499
4. Chem. Abstr. 1983, 98, 113584.
5. a) H. Hara, N. Maruyama, S. Yamashita, Y. Hayashi, K.-H. Lee, K. F. Bastow, Chairul, R. Marumoto, Y. Imakura, Chem. Pharm. Bull. 1997, 45, 1714-1716;
6. b) P. Krishnan, K. F. Bastow, Biockem. Pharmacol. 2000, 60, 1367-1379.
7. a) I. R. Green, V. I. Hugo, F. Oosthuizen, R. G. F. Giles, Synth. Commun, 1996, 26, 867-880;
8. b) G. A. Kraus, J.Li, Synlett 1993, 525-526;
9. c) G. A. Kraus, J. Li, M. Gordon, J. H. Jensen, J. Org. Chem, 1994, 59, 2219-2222.
10. a) P. P. Deshpande, K. N. Price, D. C. Baker, J. Org. Chem. 1996, 61, 455-458;
11. b) J. S. Swenton, J. N. Freskos, P. Dalidowicz, M. L. Kerns, J. Org. Chem. 1996, 61, 459-464.
12. a) P. P. Deshpande, K. N. Price, D. C. Baker, Bioorg. Med. Chem. Lett. 1995, 5, 1059-1060;
13. b) ref. 6a.
14. a) R. A. Fernandes, V. P. Chavan, A. B. Ingle, Tetrahedron Lett. 2008, 49, 6341-6343;
15. b) R. A. Fernandes, V. P. Chavan, Tetrahedron Lett. 2008, 49, 3899-3901.
16. For a similar alkyne deprotection, see: a) K. A. Korthals, W. D. Wulff, J. Am. Chem. Soc, 2008, 130, 2898-2899;
17. b) D. Boyll, F. Lopez, H. Sasaki, D. Frantz, E. M. Carreira, Org. Lett., 2000, 2, 4233-4236.
18. a) K. H. Dötz, P. Tomuschat, Chem. Soc. Rev. 1999, 28, 187-198;
19. b) K. H. Dötz, Angew. Chem. Int. Ed. Engl. 1975, 14, 644-645.
20. For similar lactaldehyde arylations, see: C. Curti, F. Zanardi, L. Battistini, A. Sartori, G. Rassu, L. Pinna, G. Casiraghi, J. Org. Chem. 2006, 71, 8552-8558.
21. R. A. Fernandes, R. Brückner, Synlett 2005, 8, 1281-1285.
22. a) J. S. Pyrek, O. Achmatowicz, A. Zamojski, Tetrahedron 1977, 33, 673-680;
23. b) M. P. DeNinno, R. Schoenleber, R. J. Perner, L. Lijewski, K. E. Asin, D. R. Britton, R. MacKenzie, J. W. Kebabian, J. Med. Chem. 1991, 34, 2561-2569;
24. c) M. P. DeNinno, R. R. J. Perner, H. E. Morton, S. DiDomenico Jr., J. Org. Chem, 1992, 57, 7115-7118;
25. d) T. Masquelin, U. Hengartner, J. Streith, Synthesis 1995, 780-786;
26. e) T. Masquelin, U. Hengartner, J. Streith, Helv. Chim, Acta 1997, 80, 43-58;
27. f) P. Contant, M. Haess, J. Riegl, M. Scalone, M. Visnick, Synthesis 1999, 821-828;
28. g) E. L. Larghi, T. S. Kaufman, Synthesis 2006, 187-220.
29. 1H NMR spectrum of the crude mixture.
30. D. Christophe, L. Bernard, E. M. Istvan, T. Bernard, D. JeanPaul, B. Justin, Tetrahedron 2004, 60, 7693-7704.