One-pot stereoselective synthesis of pyrano[3,2-c]benzothiopyrans: A new generation and [4+2] cycloaddition of ortho-thioquinonemethides

Synlett

Volumn , Issue 3, 2005, Pages 469-472

  Inoue, Seiichi ^a   Wang, Ping ^a   Nagao, Mami ^a   Hoshino, Yujiro ^a   Honda, Kiyoshi ^a  

^a YOKOHAMA NATIONAL UNIVERSITY   (Japan)

Author keywords

4+2 cycloaddition; Heterocycles; Lewis acid; Stereoselective synthesis; Sulfur

Indexed keywords

2 THIOQUINONEMETHIDE; ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; LEWIS ACID; PYRAN DERIVATIVE; PYRANO[3,2 C]BENZOTHIOPYRAN; QUINONE DERIVATIVE; SULFONIC ACID DERIVATIVE; THIOSALICYLALDEHYDE DERIVATIVE; TOLUENESULFONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 14644388125     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-862379     Document Type: Article

References (30)

1. (a) Ellis, G. P.; Lockhart, I. M. In Chromans and Tocopherols, Vol. 36; John Wiley and Sons: New York, 1981, 1-58.
2. (b) Cinganek, E. In Organic Reactions, Vol. 32; Dauben, W. G., Ed.; John Wiley and Sons: New York, 1984, 79.
3. (c) Ingal, A. H. In Comprehensive Heterocyclic Chemistry, Vol. 3; Boulton, A. S.; Mckillop, A., Eds.; Pergamon Press: Oxford, 1984, 773.
4. (d) Talley, J. J. J. Org. Chem. 1985, 50, 1695.
5. (e) Hepworth, J. D.; Heron, B. M. In Progress in Heterocyclic Chemistry, Vol. 15; Gribble, G. W.; Joule, J. A., Eds.; Pergamon Press: Amsterdam, 2003, 360-384.
6. (a) Boger, D. L.; Weinreb, S. M. In Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: New York, 1987, 193-197.
7. (b) Boger, D. L.; Weinreb, S. M. In Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: New York, 1987, 225.
8. (c) Inamoto, N. Heteroat. Chem. 2001, 12, 183.
9. (d) Okazaki, R.; Ishii, F.; Inamoto, N. Bull. Chem. Soc. Jpn. 1978, 51, 309.
10. (a) Kaye, P. T.; Nocanda, X. W. Synthesis 2001, 2389.
11. (b) Katritzky, A. R.; Button, M. A. C. J. Org. Chem. 2001, 66, 5595.
12. (c) Kumar, P.; Bodas, M. S. Tetrahedron 2001, 57, 9755.
13. (d) Ram, V. J.; Agarwal, N.; Saxena, A. S.; Farhanullah, S.; Sharon, A.; Maulik, P. R. J. Chem. Soc., Perkin Trans. 1 2002, 1426.
14. Saito, T.; Horikoshi, T.; Otani, T.; Matsuda, Y.; Karakasa, T. Tetrahedron Lett. 2003, 44, 6513.
15. Wermuth, C. G. The Practice of Medicinal Chemistry; Academic Press: London, 1996, 258.
16. (a) Inoue, S.; Asami, M.; Honda, K.; Miyazaki, H. Chem. Lett. 1996, 889.
17. (b) Miyazaki, H.; Honda, K.; Asami, M.; Inoue, S. J. Org. Chem. 1999, 64, 9507.
18. (c) Miyazaki, H.; Honda, Y.; Honda, K.; Inoue, S. Tetrahedron Lett. 2000, 41, 2643.
19. For a review of ortho-thioquinonemethide see: Inoue, S.; Honda, K. Kagaku Kogyo 2004, 55, 212; Journal written in Japanese.
20. (a) Arnoldi, A.; Carughi, M. Synthesis 1988, 155.
21. (b) Kasmai, H. S.; Mischke, S. G. Synthesis 1989, 763.
22. (c) Toste, F. D.; Lough, A. J.; Still, I. W. J. Tetrahedron Lett. 1995, 36, 6619.
23. (d) Gallagher, T.; Pardoe, D. A.; Porter, R. A. Tetrahedron Lett. 2000, 41, 5415.
24. 3): δ = 21.4, 22.2, 30.7, 33.7, 48.5, 56.1, 74.4, 78.6, 79.5, 112.3, 127.2, 127.6, 128.0, 131.6, 135.5, 141.4, 145.8.
25. Compound 6 was purified by silica gel column chromatography, and was characterized by NMR.
26. (a) Ishihara, K. In Lewis Acid Reagents; Yamamoto, H., Ed.; Oxford University Press: New York, 1999, 31-64.
27. (b) Lin, G. Q.; Li, Y. M.; Chan, A. S. C. In Principles and Applications of Asymmetric Synthesis; Wiley-Interscience: Great Britain, 2001, 267-330.
28. (c) Hayashi, Y. In Cycloaddition Reactions in Organic Synthesis; Kobayashi, S.; Jørgensen, K. A., Eds.; Wiley-VCH: Weinheim (Germany), 2002, 5-56.
29. (a) Okauchi, T.; Tanaka, T.; Minami, T. J. Org. Chem. 2001, 66, 3924.
30. (b) Yadav, J. S.; Reddy, B. V. S.; Aruna, M.; Thomas, M. Synthesis 2002, 217.