Expedient two-step synthesis of phenolic cyclitols from benzene

Journal of Organic Chemistry

Volumn 71, Issue 12, 2006, Pages 4521-4524

  Crich, David ^a   Grant, Daniel ^a   Wink, Donald J ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENESELENOL; OSMOYLATION; PHENOLIC CYCLITOLS; PHENOLIC IODIDES;

BENZENE; CATALYSIS; REACTION KINETICS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

ALCOHOLS;

1,4 CYCLOHEXADIENE; ALCOHOL; BENZENE; BENZENESELENOL; CYCLOHEXENE 1,2 DIOL DERIVATIVE; INOSITOL DERIVATIVE; IODIDE; ORGANOSELENIUM DERIVATIVE; PHENOL DERIVATIVE; PHENOLIC CYCLITOL; PHENOLIC IODIDE; TRIBUTYLTIN; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL REACTION; OSMOYLATION; RACEMIC MIXTURE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

BENZENE; CRYSTALLOGRAPHY, X-RAY; INOSITOL; PHENOLS; STEREOISOMERISM;

EID: 33744947781     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0603734     Document Type: Article

References (44)

1. (a) Posternak, T. The Cyclitols; Holden-Day: San Francisco, 1962.
2. (b) Hudlicky, T.; Cebulak, M. Cyclitols and Their Derivatives: A Handbook of Physical, Spectral, and Synthetic Data; VCH: New York, 1993.
3. (a) The Inositol Phosphates. Chemical Synthesis and Biological Significance; Billington, D. C., Ed.; VCH: New York, 1993.
4. (b) Phosphoinositides: Chemistry, Biochemistry, and Biomedical Applications; Bruzik, K. S., Ed.; ACS Symposium Series 718; American Chemical Society: Washington, DC, 1999.
5. (c) Thomas, J. R.; Dwek, R. A.; Rademacher, T. W. Biochemistry 1990, 29, 5413-5422.
6. (d) Potter, B. V. L.; Lampe, D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1933-1972.
7. (e) Sureshan, K. M.; Shashidhar, M. S.; Praveen, T.; Das, T. Chem. Rev. 2003, 103, 4477-4503.
8. (a) Kobayashi, Y. In Glycosciene: Chemistry and Biology; Fraser-Reid, B., Tatsuta, K., Thiem, J., Eds.; Springer: Berlin, 2001; Vol. 3, pp 2595-2661.
9. (b) Martínez-Grau, A.; Marco-Contelles, J. Chem. Soc. Rev. 1998, 27, 155-162.
10. (c) Carbohydrate Mimics: Concepts and Methods; Chapleur, Y., Ed.; Wiley-VCH: New York, 1998.
11. (d) Ferrier, R. J.; Middleton, S. Chem. Rev. 1993, 93, 2779-2831.
12. (e) Rassu, G.; Auzzas, L.; Pinna, L.; Battistini, L.; Curti, C. In Bioactive Natural Products (J); Atta-ur-Rahman, Ed.; Elsevier Science: New York, 2003; Vol. 29, pp 449-520.
13. McCasland, G. E.; Furuta, S.; Durham, L. J. J. Org. Chem. 1966, 31, 1516-1521.
14. (a) Martin, S. F. In The Alkaloids; Brossi, A., Ed.; Academic Press: San Diego, 1987; Vol. 30, pp 252-376.
15. (b) Polt, R. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1996; Vol. 3, pp 109-148.
16. (c) Hoshino, O. In The Alkaloids; Cordell, G. A., Ed.; Academic: New York, 1998; Vol. 51, pp 323-424.
17. (d) Jin, Z. Nat. Prod. Rep. 2003, 20, 606-614.
18. (e) Rinner, U.; Hudlicky, T. Synlett 2005, 365-405.
19. (a) Ley, S. V. Pure Appl. Chem. 1990, 62, 2031-2034.
20. (b) Carless, H. A. Tetrahedron: Asymmetry. 1992, 3, 795-826.
21. (c) Hudlicky, T.; Thorpe, A. J. J. Chem. Soc., Chem. Commun. 1996, 1993-2000.
22. (d) Hudlicky, T.; Gonzalez, D.; Gibson, D. Aldrichimica Acta 1999, 32, 35-62.
23. Motherwell, W. B.; Williams, A. S. Angew. Chem., Int. Ed. Engl. 1995, 34, 203-213.
24. (a) Angelaud, R.; Landais, Y. J. Org. Chem. 1996, 61, 5202-5203.
25. (b) Angelaud, R.; Babot, O.; Charvat, T.; Landais, Y. J. Org. Chem. 1999, 64, 9613-9624.
26. Reviews on the desymmetrization of cyclohexadienes: (a) Studer, A.; Kim, Y. H. Synlett 2005, 3033-3041.
27. (b) Rahman, N. A.; Landais, Y. Curr. Org. Chem. 2002, 6, 1369-1395.
28. Crich, D.; Hwang, J.-T. J. Org. Chem. 1998, 63, 2765-2770.
29. Scaiano, J. C.; Stewart, L. C. J. Am. Chem. Soc. 1983, 105, 3609-3614.
30. Note that most radical cyclizations onto arenes are oxidative and probably not chain reactions. (a) Engel, P. S.; Wu, W.-X. J. Am. Chem. Soc. 1989, 111, 1830-1835.
31. (b) Curran, D. P.; Yu, H.; Liu, H. Tetrahedron 1994, 50, 7343-7366.
32. (c) Curran, D. P.; Liu, H. J. Chem. Soc., Perkin Trans. 1 1994, 1377-1393.
33. (d) Beckwith, A. L. J.; Bowry, V. W.; Bowman, W. R.; Mann, E.; Parr, J.; Storey, J. M. D. Angew. Chem., Int. Ed. 2004, 43, 95-98.
34. Stannane- and silane-mediated intermolecular oxidative radical additions to arenes. (a) Núñez, A.; Sánchez, A.; Burgos, C.; Alvarez-Builla, J. Tetrahedron 2004, 60, 6217-6224.
35. (b) Martínez-Barrasa, V.; Garcia de Viedma, A.; Burgos, C.; Alvarez-Builla, J. Org. Lett. 2000, 2, 3933-3935.
36. (c) Crich, D.; Patel, M. Heterocycles 2004, 64, 499-564.
37. Newcomb, M.; Choi, S.-Y.; Horner, J. H. J. Org. Chem. 1999, 64, 1225-1231.
38. (a) Crich, D.; Yao, Q. J. Org. Chem. 1995, 60, 84-88.
39. (b) Crich, D.; Jiao, X.-Y.; Yao, Q.; Harwood, J. S. J. Org. Chem. 1996, 61, 2368-2373.
40. Crich, D.; Sannigrahi, M. Tetrahedron 2002, 58, 3319-3322.
41. Crich, D.; Rumthao, S. Tetrahedron 2004, 60, 1513-1516.
42. Crich, D.; Grant, D. J. Org. Chem. 2005, 70, 2384-2386.
43. Van Rheenan, V.; Cha, D. Y.; Hartley, W. M. Organic Syntheses; Wiley & Sons: New York, 1988; Collect. Vol. No. VI, pp 342-348.
44. Donohoe, T. J.; Blades, K.; Moore, P. R.; Waring, M. J.; Winter, J. J. G.; Helliwell, M.; Newcombe, N. J.; Stemp, G. J. Org. Chem. 2002, 67, 7946-7956.