Pectenotoxin-2 synthetic studies. 1. Alkoxide precoordination to [Rh(NBD)(DIPHOS-4)]BF4 allows directed hydrogenation of a 2,3-dihydrofuran-3-ol without competing furan production

Organic Letters

Volumn 4, Issue 6, 2002, Pages 937-940

  Paquette, Leo A ^a   Peng, Xiaowen ^a   Bondar, Dmitriy ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; FURAN DERIVATIVE; HYDROGEN; OXIDE; PECTENOTOXIN 2; PYRAN DERIVATIVE;

ARTICLE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

ANTINEOPLASTIC AGENTS; FURANS; HYDROGEN; MAGNETIC RESONANCE SPECTROSCOPY; OXIDES; PYRANS;

EID: 0037149678     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol010302l     Document Type: Article

References (42)

1. (1)(a) Yasumoto, T.; Murata, M.; Oshima, Y.; Sano, M.; Matsumoto, G. K.; Clardy, J. Tetrahedron 1985, 41, 1019.
2. (b) Murata, M.; Sano, M.; Iwashita, T.; Naoki, H.; Yasumoto, T. Agric. Biol. Chem. 1986, 50, 2693.
3. (c) Yasumoto, T.; Murata, M.; Lee, J.-S.; Torigoe, K. Mycotoxins and Phwotoxins 1989, 88, 375.
4. (d) Yasumoto, T.; Murata, M. Chem. Rev. 1993, 93, 1897.
5. (e) Sasaki, K.; Wright, J. L. C.; Yasumoto, T. J. Org. Chem. 1998, 63, 2475.
6. Ishige, M.; Satoh, N.; Yasumoto, T. Reps. Hokkaido Inst. Health 1988, 38, 15.
7. Jung, J. H.; Sim, C. J.; Lee, C.-O. J. Nat. Prod. 1995, 58, 1722.
8. Spector, I.; Braet, F.; Shochet, N. R.; Bubb, M. R. Microscop. Res. Technol. 1999, 47, 18.
9. (a) Amano, S.; Fujiwara, K.; Murai, A. Synlett 1997, 1300.
10. (b) Awakura, D.; Fujiwara, K.; Murai, A. Synlett 2000, 1733.
11. Micalizio, G. C.; Roush, W. R. Org. Lett. 2001, 3, 1949.
12. (a) Paquette, L. A.; Pissarnitski, D.; Barriault, L. J. Org. Chem. 1998, 63, 7389.
13. (b) Paquette, L. A.; Barriault, L.; Pissarnitski, D. J. Am. Chem. Soc. 1999, 121, 4542.
14. (c) Barriault, L.; Boulet, S. L.; Fujiwara, K.; Murai, A.; Paquette, L. A.; Yotsu-Yamashita, M. Bioorg. Medicin. Chem. Lett. 1999, 9, 2069.
15. (d) Paquette, L. A.; Barriault, L.; Pissarnitski, D.; Johnston, J. N. J. Am. Chem Soc. 2000, 122, 619.
16. Liu, J.; Paquette, L. A. Unpublished work.
17. (a) Raimundo, B. C.; Heathcock, C. H. Synlert 1995, 1213.
18. (b) Yang, J.; Cohn, S. T.; Romo, D. Org. Lett. 2000, 2, 763.
19. (c) Walker, M. A.; Heathcock, C. H. J. Org. Chem. 1991, 56, 5747.
20. (d) Danda, H.; Hansen, M. M.; Heathcock, C. H. J. Org. Chem. 1990, 55, 173.
21. (a) Gage, J. R.; Evans, D. A. Org. Synth. 1990, 68, 77.
22. (b) Gage, J. R.; Evans, D. A. Org. Synth. 1990, 68, 83.
23. (a) Evans, D. A.; Nelson, J. V.; Vogel, E.; Taber, T. R. J. Am. Chem. Soc. 1981, 103, 3099.
24. (b) Inoue, T.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1980, 53, 174.
25. Prashad, M.; Har, D.; Kim, H.-Y.; Repic, O. Tetrahedron Lett. 1998, 39, 7067.
26. (a) Ghosh, A. K.; McKee, S. P.; Thompson, W. J. J. Org. Chem. 1991, 56, 6500.
27. (b) Freudenberg, K.; Wolf, A. Chem. Ber. 1927, 60, 232.
28. (c) Ireland, R. E.; Thaisrivongs, S.; Vanier, N.; Wilcox, C. S. J. Org. Chem. 1980, 45, 48.
29. (d) Ireland, R. E.; Norbeck, D. W.; Mandel, G. S.; Mandel, N. S. J. Am. Chem. Soc. 1985, 107, 3285.
30. Parker, K. A.; Su, D.-S. J. Org. Chem. 1996, 67, 2191.
31. Lipshutz, B. H.; Pegram, J. J. Tetrahedron Lett. 1980, 21, 3343.
32. This assignment is in line with predominant adherence to the Cram chelate transition state during 1,2-addition to the α-chiral, α-oxygenated aldehyde 10. (17) (a) For a review, see: Brown, J. M. Angew. Chem., Int. Ed. Engl. 1987, 26, 190.
33. (b) Smith, M. E. B.; Derrien, N.; Lloyd, M. C.; Taylor, S. J. C.; Chaplin, D. A.; McCague, R. Tetrahedron Lett. 2001, 42, 1347.
34. (a) Evans, D. A.; Morrissey, M. M. J. Am. Chem. Soc. 1984, 106, 3866.
35. (b) Brown, J. M.; Naik, R. G. J. Chem. Soc., Chem. Commun. 1982, 348.
36. (a) Crabtree, R. H.; Davis, M. W. J. Org. Chem. 1986, 51, 2655.
37. (b) Stork, G.; Kahne, D. E. J. Am. Chem. Soc. 1983, 105, 1072.
38. Thompson, H. W.; McPherson, E. J. Am. Chem. Soc. 1974, 96, 6232.
39. Zhong, Y.-L.; Shing, T. K. M. J. Org. Chem. 1997, 62, 2622.
40. Wadsworth, W. S., Jr. Org. React. 1977, 25, 73.
41. Oikawa, Y.; Yoshioka, T.; Yonemitsu, O. Tetrahedron Lett. 1982, 23, 885.
42. 4 (13.5 mg, 20 mol %) in deoxygenated THF (1.5 mL) was quickly introduced. The vial was placed in a Parr autoclave, flushed with argon, and pressurized to 800-900 psi of hydrogen. After overnight stirring (17 h). the pressure was released and the reaction mixture was subjected directly to chromatography on silica gel (elution with 2:1 hexanes/ethyl acetate).