Stereoselective Synthesis of cis- And irans-2,3-Disubstituted Tetrahydrofurans via Oxonium-Prins Cyclization: Access to the Cordigol Ring System

Organic Letters

Volumn 12, Issue 5, 2010, Pages 900-903

  Spivey, Alan C ^a   Laraia, Luca ^a   Bayly, Andrew R ^a   Rzepa, Henry S ^a   White, Andrew J P ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77749286121     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol9024259     Document Type: Article

References (55)

1. For an excellent review, see: (a) Snider, B. B. In Comprehensive Organic Synthesis; Trost. B. M., Fleming. I., Heathcock, C. H., Eds.; Pergamon Press: New York. 1991: Vol. 2, pp 527-561. See also:
2. (b) Wolfe, J. P.: Hay. M. B. Tetrahedron 2007, 63, 261.
3. (c) Clarke, P. A.; Santos, S. Eur: J. Org. Chem. 2006, 2045.
4. This classification was introduced by Oppolzer and Snieckus; see: (a) Oppolzer, W.; Snieckus, V. Angew. Chem., Int. Ed. Engl. 1978, 17, 476. More recently, Mikami has proposed an alternative nomenclature; see:
5. (b) Mikami, K.; Sawa. E.; Terada. M. Tetrahedron: Asymmetry 1991, 2, 1403.
6. (c) Mikami, K.; Shimizu, M. Chem. Rev. 1992, 1021.
7. For THP formation, see, e.g.: (a) Zhou, H.; Loh, T.-P. Tetrahedron Lett. 2009, 50, 4368.
8. (b) Reddv. U. C.; Bondalapati. S.; Saikia. A. K. J. Org. Chem. 2009, 74, 2605.
9. (c) Yadav, J. S.; Chakravarthy. P. P.; Borkar, P.; Reddy, B. V. S.; Sarma, A. V. S. Tetrahedron Lett. 2009, 50, 5998.
10. (d) Yadav, J. S.; Reddv. B. V. S.; Reddv, Y. J.; Reddv. N. S. Tetrahedron Lett. 2009, 50, 2877.
11. (e) Liu. F.; Loh, T.-P. Org. Lett. 2007, 9, 2063.
12. (f) Chan, K.-P.; Loh, T.-P. Org. Lett. 2005, 7, 4491.
13. (g) Lowe, J. T.; Panek, J. S. Org. Lett. 2005, 7, 3231.
14. (h) Barry, C. S. J.; Crosby, S. R.; Harding, J. R.: Hughes, R. A.; King. C. D.; Parker. G. D.; Willis, C. L. Org. Lett. 2003, 5, 2429.
15. (i) Hoye, T. R.; Hu, M. J. Am. Chem. Soc. 2003, 125, 9576.
16. (j) Marumoto, S.; Jaber, J. J.; Vitale, J. P.; Rychnovsky, S. D. Org. Lett. 2002, 4, 3919.
17. For THF formation, see, e.g.: (a) Ünaldi, S.; Özlügedik, M.; Fröhlich, R.; Hoppe, D. Adv. Synth. Catal. 2005, 347, 162.
18. (b) Sarkar, T. K.; Haque, S. A.; Basak, A. Angew. Chem., Int. Ed. 2004, 43, 1417.
19. (c) Loh, T.-P.; Hu, Q.-Y.; Tan, K.-T.; Cheng, H.-S. Org. Lett. 2001, 3, 2669.
20. (d) Loh, T.-P.; Hu, Q.-Y.; Ma, L.-T. J. Am. Chem. Soc. 2001, 123, 2450.
21. (e) Hoppe, D.; Krämer, T.; Erdbrügger, C. F.; Egert, E. Tetrahedron Lett. 1989, 30, 1233.
22. See, e.g.: (a) Jasti, R.; Rychnovsky, S. D. J. Am. Chem. Soc. 2006, 128, 13640.
23. (b) Vitale, J. P.; Wolckenhauer, S. A.; Do, N. M.; Rychnovsky, S. D. Org. Lett. 2005, 7, 3255.
24. (c) Dalgard, J. E.; Rychnovsky, S. D. Org. Lett. 2005, 7, 1589.
25. (d) Rychnovsky, S. D.; Thomas, C. R. Org. Lett. 2000, 2, 1217,
26. See, e.g.: Chen, C.; Mariano, P. S. J. Org. Chem. 2000, 65, 3252.
27. See, e.g.: (a) Aubele, D. L.; Wan., S.; Floreancig, P. E. Angew. Chem., Int. Ed. 2005, 44, 3485.
28. (b) Smith, A. B., III.; Safonov, I.; Corbett, R. M. J. Am. Chem. Soc. 2002, 124, 11102.
29. (c) Smith, A. B., III; Safonov, I.; Corbett, R. M. J. Am. Chem. Soc. 2001, 123, 12426.
30. (d) Smith, A. B., III.; Minbiole, K. P.; Verhoest, P. R.; Schelhaas, M. J. Am. Chem. Soc. 2001, 123, 10942.
31. (e) Takano, S.; Samizu, K.; Ogasawara, K. Synlett 1993, 785.
32. (f) Takano, S.; Samizu, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1993, 1032.
33. See, e.g.: (a) Overman, L. E.; Pennington, L. D. J. Org. Chem. 2003, 68, 7143.
34. (b) Hanaki, N.; Link, J. T.; MacMillan, D. W. C.; Overman, L. E.; Trankle, W. G.; Wurster, J. A. Org. Lett. 2000, 2, 223. Note: These oxonium-Prins reactions give ring closure to a THP cation (cf. A, Scheme 1) which undergoes pinacol rearrangement to a THF final product.
35. (a) Miles, S. M.; Marsden, S. P.; Leatherbarrow, R. J.; Coates, W. J. J. Org. Chem. 2004, 69, 6874.
36. (b) Miles, S. M.; Marsden, S. P.; Leatherbarrow, R. J.; Coates, W. J. Chem. Commun. 2004, 2292.
37. (c) Cassidy, J. H.; Marsden, S. P.; Stemp, G. Synlett 1997, 1411.
38. (d) Meyer, C.; Cossy, J. Tetrahedron Lett. 1997, 38, 7861.
39. Racemisation via various mechanisms can plague oxonium-Prins reactions involving homoallyic alcohols; see ref 5a and references cited therein.
40. Charette, A. B.; Juteau, H.; Lebel, H.; Molinaro, C. J. Am. Chem. Soc. 1998, 120, 11943.
41. TMSBr appears to serve as a bromide source (cf. ref 3e). Trace product formation occurred using only TMSBr as promoter.
42. The isomeric ratios were unchanged after resubjection to the reaction conditions (Table 2, entry 7), suggesting the products are formed under kinetic control.
43. 4, cf. Khurana, J. M.; Kumar, S.; Nand, B. Can. J. Chem. 2008, 86, 1052). The results were consistent with the assignments made by NOESY. For example, di-debromination of 5a and 5c gave the same products as mono-debromination of 4a/b and 4c, respectively (compounds 12 and 11, see the Supporting Information).
44. That these TSs are likely to be close in energy is consistent with our calculations on the formation of compound 10; see ref 21.
45. See, e.g.: Craig, D.; Meadows, J. D.; Pécheux, M. Tetrahedron Lett. 1998, 59, 141.
46. For the isolation and characterization of cordigol, see: Marston, A.; Zagorski, M. G.; Hostettmann, K. Helv. Chim. Acta 1988, 71, 1210.
47. The same core ring system is also found in the Lophira lanceolata natural product lophirone H; see: Tih, R. G.; Sondengam, B. L.; Martin, M. T.; Bodo, B. Phytochemistry 1990, 29, 2289.
48. 4 led to the formation of a mixture of compound 10 (40% yield) and a product tentatively assigned as that of intermolecular trapping by bromide (19% yield). This result is consistent with an oxonium-Prins pathway.
49. See: (a) Miyazaki, H.; Honda, K.; Asami, M.; Inoue, S. J. Org. Chem. 1999, 64, 9507. Related transformations have been used to form pyrano[2,3-c]benzopyrans; see:
50. (b) Yadav, J. S.; Reddy, B. V. S.; Sadashiv, K.; Padmavani, B. Adv. Synth. Catal. 2004, 346, 607.
51. Yadav, J. S.; Reddy, B. V. S.; Aruna, M.; Thomas, M. Synthesis 2002, 217. Related transformations have been used to form pyrano[2,3-c]benzothiopyrans, see:
52. Inoue, S.; Wang, P.; Nagao, M.; Hoshino, Y.; Honda, K. Synlett 2005, 469.
53. (e) Saito, T.; Horikoshi, T.; Otani, T.; Matsuda, Y.; Karakasa, T. Tetrahedron Lett. 2003, 44, 6513.
54. For an excellent review of o-quinonemethide chemistry, see: Van. De Water, R. W.; Pettus, T. R. R. Tetrahedron 2002, 58, 5367.
55. trans