The carbohydrate-sesquiterpene interface. Directed synthetic routes to both (+)- and (-)-fomannosin from D-glucose

Journal of Organic Chemistry

Volumn 73, Issue 12, 2008, Pages 4548-4558

  Paquette, Leo A ^a   Peng, Xiaowen ^a   Yang, Jiong ^a,b   Kang, Ho Jung ^a,c  

^a OHIO STATE UNIVERSITY   (United States)

^b TEXAS A AND M UNIVERSITY   (United States)

^c Kyung Hee University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATES; CHEMICAL REACTIONS; COMPUTER NETWORKS; ESTERS; GLUCOSE; MICROFLUIDICS; ORGANIC COMPOUNDS; ZIRCONIUM COMPOUNDS;

(BUTADIENE)ZIRCONOCENE; CHEMICAL EQUATIONS; CHEMICAL SYNTHESES; CHEMOSELECTIVE REDUCTIONS; CYCLOBUTANOLS; D-GLUCOSE; DIHYDROXYLATION; MALONIC ESTER; RING CLOSING METATHESIS (RCM); RING-CONTRACTION; SESQUITERPENE; SYNTHETIC ROUTES;

SYNTHESIS (CHEMICAL);

BUTANOL; CARBOHYDRATE; CYCLOBUTANE DERIVATIVE; ESTER DERIVATIVE; FOMANNOSIN; GLUCOSE; HYDROXYL GROUP; LACTONE; MALONIC ACID DERIVATIVE; OSMIUM DERIVATIVE; SESQUITERPENE; SULFITE; TRIFLUOROMETHANESULFONIC ACID; VINYL DERIVATIVE; ZIRCONOCENE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; DIHYDROXYLATION; ELIMINATION REACTION; ENANTIOMER; OPTICAL ROTATION; REACTION ANALYSIS; REDUCTION; RING CLOSING METATHESIS; STEREOCHEMISTRY; SYNTHESIS;

CYCLIZATION; GLUCOSE; LACTONES; MAGNETIC RESONANCE SPECTROSCOPY; SESQUITERPENES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, INFRARED; STEREOISOMERISM;

EID: 45249090828     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8004233     Document Type: Article

References (87)

1. Bassett, C.; Underwood, R. T.; Kepler, J. A.; Hamilton, P. B. Phytopathology 1967, 57, 1046.
2. Kepler, J. A.; Wall, M. S.; Mason, J. E.; Bassett, C.; McPhail, A. T.; Sim, G. A. J. Am. Chem. Soc. 1967, 89, 1260.
3. Cane, D. E.; Nachbar, R. B.; Clardy, J.; Finer, J. Tetrahedron Lett. 1977, 4277.
4. (a) Cane, D.; Nachbar, R. B. Tetrahedron Lett. 1976, 2097.
5. (b) Cane, D.; Nachbar, R. B. J. Am. Chem. Soc. 1978, 100, 3208.
6. Miyano, K.; Ohfune, Y.; Azurne, S.; Matsumoto, T. Tetrahedron Lett. 1974, 1545.
7. (a) Kosugi, H.; Uda, H. Bull. Chem. Soc. Jpn. 1980, 53, 160.
8. (b) Kosugi, H.; Uda, H. Chem. Lett. 1977, 1491.
9. (a) Semmelhack, M. F.; Tomoda, S.; Nagaoka, H.; Boelter, S. D.; Hurst, K. M. J. Am. Chem. Soc. 1982, 104, 747.
10. (b) Semmelhack, M. F.; Tomoka, S. J. Am. Chem. Soc. 1981, 103, 2427.
11. (c) Semmelhack, M. F. Strategies Tactics Org. Synth. 1984, 201-222.
12. (a) Paquette, L. A.; Peng, X.; Yang, J. Angew. Chem., Int. Ed. 2007, 46, 7817.
13. (b) Paquette, L. A.; Kang, H.-J. Tetrahedron 2004, 60, 1353.
14. Negishi, E.; Cederbaum, F. E.; Takahashi, T. Tetrahedron Lett. 1986, 27, 2829.
15. (a) Ito, H.; Motoki, Y.; Taguchi, T.; Hanzawa, Y. J. Am. Chem. Soc. 1993, 115, 8835.
16. (b) Hanzawa, Y.; Ito, H.; Taguchi, T. Synlett 1995, 299.
17. (a) Paquette, L. A.; Cuniere, N. Org. Lett. 2002, 4, 1927.
18. (b) Paquette, L. A.; Kim, I. H.; Cuniere, N. Org. Lett. 2003, 5, 221.
19. (a) Schmidt, O. T. Methods Carbohydr. Chem. 1963, 2, 320.
20. (b) Hwang, C. K.; Li, W. S.; Nicolaou, K. C. Tetrahedron Lett. 1984, 25, 2295.
21. Just, G.; Luthe, C. Can. J. Chem. 1980, 58, 2286.
22. Williams, D. R.; Klingler, F. D.; Allen, E. E.; Lichtenthaler, F. W. Tetrahedron Lett. 1988, 29, 5087.
23. Hase,T.; Wähälä, K. Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: Chichester, 1995; Vol. 7, pp 4533-4534.
24. (a) Overman, L. E. Acc. Chem. Res. 1980, 13, 218.
25. (b) Patil, V. J. Tetrahedron Lett. 1996, 37, 1481.
26. Schlosser, M.; Jenny, T.; Guggisberg, Y. Synlett 1990, 704.
27. 8b
28. (a) Danheiser, R. L.; Savariar, S.; Cha, D. D. Org. Synth. 1990, 68, 32.
29. (b) Johnston, B. D.; Czyzervska, E.; Oehlschlager, A. C. J. Org. Chem. 1987, 52, 3693.
30. (C) Mehta, G.; Rao, H. S. P. Synth. Commun. 1985, 991.
31. (d) Krepski, L. R.; Hessner, A. J. Org. Chem. 1978, 43, 2879.
32. (e) Greene, A. E.; Luche, M. J.; Depres, J.-P. J. Am. Chem. Soc. 1983, 105, 2435.
33. (a) McMurry, J. E.; Lectka, T.; Rico, J. G. J. Org. Chem. 1989, 54, 3748.
34. (b) McMurry, J. R. Chem. Rev. 1989, 89, 1513.
35. (c) Lectka, T. In Active Metals; Fürstner,A., Ed.; Wiley-VCH: Weinheim, 1995; p 85.
36. (a) McMurry, J. E.; Lectka, T.; Rico, J. G. Tetrahedron Lett. 1989, 30, 1169.
37. (b) Robertson, G. M. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; p 563.
38. Fuji, K.; Nakano, S.; Fujita, E. Synthesis 1975, 276.
39. (a) Reviews: Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
40. (b) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012.
41. (c) Roy, R.; Das, S. K. Chem. Commun. 2000, 519.
42. (d) Philips, A. J.; Arbell, A. D. Aldrichchim. Acta 1999, 32, 75.
43. (e) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371.
44. (f) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
45. (g) Ivin, K. J. J. Mol. Catal. A 1998, 133, 1.
46. (h) Alkene Metathesis in Organic Synthesis; Fürstner, A., Ed.; Springer: Berlin, 1998.
47. (i) Randall, M. L.; Snapper, M. L. J. Mol. Catal. A 1998, 113, 29.
48. (j) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1991, 36, 2036.
49. (a) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039.
50. (b) Schwab, P.; Grubbs, R. H.; Ziller, J. W. Angew. Chem., Int. Ed. Engl. 1996, 118, 100.
51. (a) Schrock, R. L. R.; Murdzek, J. S.; Bazan, G. C.; Robbins, J.; Dimare, M.; O'Regan, M. B. J. Am. Chem. Soc. 1990, 112, 3875.
52. (b) Bazan, G. C.; Khosravi, E.; Schrock, R. R.; Feast, W. J.; Gibson, V. C.; O'Regan, M. B.; Thomas, J. K.; Davis, W. M. J. Am. Chem. Soc. 1990, 112, 8378.
53. (c) Bazan, G. C.; Oskam, J. H.; Cho, H. N.; Park, L. Y.; Schrock, R. R. J. Am. Chem. Soc. 1991, 113, 6899.
54. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953.
55. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; John Wiley & Sons, Inc.: New York, 1999; p 41.
56. (a) Maercker, A. Org React. 1965, 14, 270.
57. (b) Maryanoff, B. E.; Reits, A. B. Chem. Rev. 1989, 89, 863.
58. Review Pine, S. H. Org. React. 1993, 43, 1.
59. Matsubara, S.; Sugihara, M.; Utimoto, K. Synlett 1998, 313, and references cited therein.
60. Review: Ager, D. J. Org. React. 1990, 38, 1.
61. Sommer, L. H.; Mitch, F. A.; Goldberg, G. M. J. Am. Chem. Soc. 1949, 72, 2746.
62. Scouten, G. G.; Brown, H. C. J. Org. Chem. 1973, 38, 4092.
63. Review Beletskaya, I.; Pelter, A. Tetrahedron 1997, 4957.
64. (a) Reviews: Pelter, A.; Smith, K.; Brown, H. C. Borane Reagents; Academic Press: New York, 1988.
65. (b) Brown, H. C. Boranes in Organic Chemistry; Cornell University Press: Ithaca, NY, 1972.
66. (c) Brown, H. C. Organic Syntheses via Boranes; Wiley: New York, 1975.
67. (d) Cragg, G. M. L. Organoboranes in Organic Synthesis; Marcel Dekker: New York, 1973.
68. This was not the case with 2-iodoxybenzoic acid, which was prone to overoxidize 38 despite claims to the contrary: Frigerio, M.; Santagostino, M. Tetrahedron Lett. 1994, 35, 8019.
69. Review: Molander, G. A. Org. React. 1994, 46, 211.
70. (a) Imamoto, T.; Kodera, M.; Yokoyama, M. Bull. Chem. Soc. Jpn. 1982, 55, 2303.
71. (b) Beaulieu, P. L.; Deziel, R.; Brunet, M. L.; Moss, N.; Plante,R. U.S. cont.-in-part of U.S. 5,574,015, 1998, 24 pp.
72. Oliver, S. F.; Högenauer, K.; Simic, O.; Antonello, A.; Smith, M. D.; Ley, S. V. Angew. Chem., Int. Ed. 2003, 42, 5996.
73. (a) Takayama, H.; Fujiwara, R.; Kasai, Y.; Kitajima, M.; Aimi, N. Org. Lett. 2003, 5, 2967.
74. (b) Fukuyama, T.; Lin, S.-C.; Li, L. J. Am. Chem. Soc. 1990, 112, 7050.
75. (a) Fujii, H.; Hirano, N.; Uchiro, H.; Kawamura, K.; Nagase, H. Chem. Pharm. Bull. 2004, 52, 747.
76. (b) Rabiczko, J.; Urbanczyk-Lipkowska, Z.; Chemielewski, M. Tetrahedron 2002, 58, 1433.
77. Askin, D.; Angst, D.; Danishefsky, S. J. J. Org. Chem. 1987, 52, 622.
78. Cox, C.; Danishefsky, S. J. Org. Lett. 2001, 3, 2899.
79. (a) Hodgson, R.; Mahid, T.; Nelson, A. Chem. Commun. 2001, 2076.
80. (b) Donohoe, T. J.; Fisher, J. W.; Edwards, P. J. Org. Lett. 2004, 6, 465.
81. White, J. D.; Somers, T. C. J. Am. Chem. Soc. 1987, 109, 4424.
82. Wang, Y.; Babirad, S. A.; Kishi, Y. J. Org. Chem. 1992, 57, 468.
83. Blakemore, P. R.; Kim, S.-K.; Schulze, V. K.; White, J. D.; Yokochi, A. F. T. J. Chem. Soc., Perkin Trans. 1 2001, 1831.
84. (a) Yan, L.; Kahne, D. Synlett 1995, 523.
85. (b) Bonzide, A.; Sauvé, G. Tetrahedron Lett. 1999, 40, 2883.
86. (a) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
87. (b) Bennani, Y. L.; Sharpless, K. B. Tetrahedron Lett. 1993, 34, 2083.