A double oxidation procedure for the preparation of halogen-substituted para-benzoquinone monoketals: Asymmetric synthesis of (-)-harveynone

Tetrahedron Letters

Volumn 51, Issue 50, 2010, Pages 6619-6621

  Hookins, Daniel R ^a   Taylor, Richard J K ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 BENZOQUINONE DERIVATIVE; HALOPHENOL; HARVEYNONE; IODINE; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; DEPROTECTION REACTION; OXIDATION;

EID: 78650237766     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.10.047     Document Type: Article

References (36)

1. Gautier, E. C. L.; Lewis, N. J.; McKillop, A.; Taylor, R. J. K. Tetrahedron Lett. 1994, 35, 8759-8760.
2. Graham, A. E.; McKerrecher, D.; Davies, D. H.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37, 7445-7448.
3. Graham, A. E.; Taylor, R. J. K. J. Chem. Soc., Perkin. Trans. 1 1997, 1087-1089.
4. Barros, M. T.; Maycock, C. D.; Ventura, M. R. Chem. Eur. J. 2000, 6, 3991-3996.
5. Bardhan, S.; Schmitt, D. C.; Porco, J. A., Jr Org. Lett. 2006, 8, 927-930.
6. Su, S.; Lei, X.; Bardhan, S.; Porco, J. A., Jr; Rychnovsky, S. D. Angew. Chem., Int. Ed. 2006, 45, 5790-5792.
7. (a) Lee, M. Y.; Kim, K. H.; Jiang, S.; Jung, Y. H.; Sim, J. Y.; Hwang, G.-S.; Ryu, D. H. Tetrahedron Lett. 2008, 49, 1965-1967;
8. (b) Mehta, G.; Islam, K. Tetrahedron Lett. 2003, 44, 6733-6736. and references therein.
9. (a) Lei, X.; Johnson, R. P.; Porco, J. A., Jr Angew. Chem., Int. Ed. 2003, 42, 3913-3917;
10. (b) Moses, J. E.; Commeiras, L.; Baldwin, J. E.; Adlington, R. M. Org. Lett. 2003, 5, 2987-2988;
11. Commeiras, L.; Moses, J. E.; Adlington, R. M.; Baldwin, J. E.; Cowley, A. R.; Baker, C. M.; Albrecht, B.; Grant, G. H. Tetrahedron 2006, 62, 9892-9901.
12. For alternative approaches to these and related natural products, see: (a) Labora, M.; Pandolfi, E. M.; Schapiro, V. Tetrahedron: Asymmetry 2010, 21, 153-155;
13. (b) Pinkerton, D. M.; Banwell, M. G.; Willis, A. C. Org. Lett. 2009, 11, 4290-4293;
14. Miller, M. W.; Johnson, C. R. J. Org. Chem. 1997, 62, 1582-1583.
15. (a) Manning, M. J.; Reynolds, P. W.; Swenton, J. S. J. Am. Chem. Soc. 1976, 98, 5008-5009;
16. (b) Gautier, E. C. L.; Lewis, N. J.; McKillop, A.; Taylor, R. J. K. Synth. Commun. 1994, 24, 2989-3008.
17. (a) McKillop, A.; Perry, D. H.; Edwards, M. J. Org. Chem. 1976, 41, 282-287;
18. (b) Pelter, A.; Elgendy, S. M. A. J. Chem. Soc., Perkin Trans. 1 1993, 1891-1896.
19. Camps, P.; González, A.; Muñoz-Torrero, D.; Simon, M.; Zúñiga, A.; Martins, M. A.; Font-Bardia, M.; Solans, X. Tetrahedron 2000, 56, 8141-8151.
20. To the best of our knowledge, the one published example in this area involves the oxidation of a pentasubstituted phenol: Clive, D. L. J.; Yu, M. Chem. Commun. 2002, 2380-2381.
21. McKillop, A.; McLaren, L.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. 1 1994, 2047-2048.
22. For a recent review on the use of hypervalent iodine reagents in natural product synthesis, see: Pouységu, L.; Deffieux, D.; Quideau, S. Tetrahedron 2010, 66, 2235-2261.
23. All compounds were fully characterised spectroscopically and by HRMS.
24. 3 requires C, 34.31; H, 3.24).
25. Henton, D. R.; Anderson, K.; Manning, M. J.; Swenton, J. S. J. Org. Chem. 1980, 45, 3422-3433.
26. Carreño, M. C.; Ribagorda, M. J. Org. Chem. 2000, 65, 1231-1234.
27. Iguchi, M.; Atsuko, N.; Hideo, E.; Koji, O.; Shosuke, Y.; Yoshinobu, K. Chem. Pharm. Bull. 1986, 34, 4910-4915.
28. Kawazu, K.; Kobayashi, A.; Oe, K. Patent JP, 0341075, 1991; Chem. Abstr. 1991, 115, 181517k.
29. Nagata, T.; Ando, Y.; Hirota, A. Biosci. Biochem. Biotech. 1992, 56, 810-811.
30. Kamikubo, T.; Ogasawara, K. Heterocycles 1998, 47, 69-72.
31. Negishi, E.-C.; Tan, Z.; Liou, S.-Y.; Liao, B. Tetrahedron 2000, 56, 10197-10208.
32. (a) Li, J.; Park, S.; Miller, R. L.; Lee, D. Org. Lett. 2009, 11, 571-574;
33. (b) Jin, M. Y.; Hwang, G.-S.; Chae, H. I.; Jung, S. H.; Ryu, D. H. Bull. Korean Chem. Soc. 2010, 31, 727-730.
34. Li, C.; Pace, E. A.; Liang, M.-C.; Lobkovsky, E.; Gilmore, T. D.; Porco, J. A., Jr J. Am. Chem. Soc. 2001, 123, 11308-11309.
35. Gautier, E. C. L.; Graham, A. E.; McKillop, A.; Standen, S. P.; Taylor, R. J. K. Tetrahedron Lett. 1997, 38, 1881-1884.
36. 23