Efficient and stereoselective syntheses of DAB-1 and D-fagomine via chiral 1,3-oxazine

Tetrahedron

Volumn 67, Issue 48, 2011, Pages 9426-9432

  Kim, Ji Yeon ^a   Mu, Yu ^a   Jin, Xiangdan ^a   Park, Seok Hwi ^a   Pham, Van Thoai ^a   Song, Dong Keun ^a   Lee, Kee Young ^b   Ham, Won Hun ^a  

^a Sungkyunkwan University   (South Korea)

^b Yongjin Fine Chemical Co Ltd   (South Korea)

Author keywords

Catalytic hydrogenation; D Fagomine; DAB 1; Natural product; Oxazine; Pd(0) catalyst

Indexed keywords

1,3 OXAZINE DERIVATIVE; 1,4 DIDEOXY 1,4 IMIDO D ARABINITOL; 2 HYDROXYMETHYLPIPERIDINE 3,4 DIOL; FAGOMINE; GLYCOSIDASE INHIBITOR; PALLADIUM; PIPERIDINE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; HYDROGENATION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 80054862042     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.09.084     Document Type: Article

References (46)

1. (a) Jones, D.W. C.; Nash, R. J.; Bell, E. A.; William, J. M. Tetrahedron Lett. 1985, 26, 3125;
2. (b) Nash, R. J.; Bell, E. A.; Williams, J. M. Phytochemistry 1985, 24, 1620;
3. (c) Furukawa, J.; Okuda, S.; Saito, K.; Hatatanaka, S. I. Phytochemistry 1985, 24, 593.
4. (a) Fleet, G. W. J.; Karpas, A.; Dwek, R. A.; Fellows, L. E.; Tyms, A. S.; Petursson, S.; Namgoong, S. K.; Ramsden, N. G.; Smith, P.W.; Son, J. C.; Wilson, F. X.; Witty, D. R.; Jacob, G. S.; Rademacher, T. W. FEBS Lett. 1988, 237, 128;
5. (b) Behling, J. R.; Campbell, A. L.; Babiak, K. A.; Ng, J. S.; Medich, J.; Farid, P.; Fleet, G. W. J. Tetrahedron 1993, 49, 3359;
6. (c) Asano, N.; Kizu, H.; Oseki, K.; Tomioka, E.; Matsui, K.; Okamoto, M.; Baba, M. J. Med. Chem. 1995, 38, 2349;
7. (d) Legler, G. In Iminosugars as Glycosidase Inhibitors: Nojirimycin and Beyond; Stütz, A. E., Ed.; Wiley-VCH: Weinheim, 1999; p 50.
8. (a) Koyama, M.; Sakamura, S. Agric. Biol. Chem. 1974, 38, 1111;
9. (b) Meyers, A. I.; Andres, C. J.; Resek, J. E.;Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; price, D. A. Tetrahedron 1999, 55, 8931;
10. (c) Lillelund, V. H.; Jensen, H. H.; Liang, X.; Bols, M. Chem. Rev. 2002, 102, 515.
11. (a) Scofield, A. M.; Fellows, L. E.; Nash, R. J.; Fleet, G. W. J. Life Sci. 1986, 39, 645;
12. (b) Kato, A.,; Asano, N.; Kizu, H.; Matsui, K.;Watson, A. A.; Nash, R. J. J. Nat. Prod. 1997, 60, 312.
13. (a) Nojima, H.; Kimura, I.; Fu-Jin, C.; Sugiura, Y.; Haruno, M.,; Kato, A.; Asano, N. J. Nat. Prod. 1998, 61, 397;
14. (b) Taniguchi, S.; Asano, N.; Tomino, F.; Miwa, I. Horm. Metab. Res. 1998, 30, 679.
15. For the syntheses of DAB-1(1), see: (a) Merino, P.; Delso, I.; Tejero, T.; Cardona, F.; Marradi, M.; Faggi, E.; Parmeggiani, C.; Goti, A. Eur. J. Org. Chem. 2008, 2929;
16. (b) Kim, I. S.; Zee, O. P.; Jung, Y. H. Org. Lett. 2006, 8, 4101;
17. (c) Lauritsen, A.; Madsen, R. Org. Biomol. Chem. 2006, 4, 2898;
18. (d) Ayad, T.; Génisson, Y.; Broussy, S.; Baltas, M.; Gorrichon, L. Eur. J. Org. Chem. 2003, 2903;
19. (e) Hulme, A. N.; Montgomery, C. H.; Henderson, D. K. J. Chem. Soc., Perkin Trans. 1 2000, 1837;
20. (f) Kim, J. H.; Yang, M. S.; Lee, W. S.; Park, K. H. J. Chem. Soc., Perkin Trans. 1 1998, 2877;
21. (g) Ahn, K. H.; Shin, Y. S. Bull. Korean Chem. Soc. 1997, 18, 1192;
22. (h) Kim, Y. J.; Kido, M.; Bando, M.; Kitahara, T. Tetrahedron 1997, 53, 7501;
23. (i) Huwe, C. M.; Blechert, S. Synthesis 1997, 61;
24. (j) Overkleeft, H. S.; van Wiltenburg, J.; Pandit, U. K. Tetrahedron 1994, 50, 4215;
25. (k) Griffat-Brunet, D.; Langlois, N. Tetrahedron Lett. 1994, 35, 2889;
26. (l) Hung, R. R.; Straub, J. A.; Whitesides, G. M. J. Org. Chem. 1991, 56, 3849;
27. (m) Fleet, G. W. J.; Witty, D. R. Tetrahedron: Asymmetry 1990, 1, 119;
28. (n) von der Osten, C. H.; Sinskey, A. J.; Barbas, C. F., III; Pederson, R. L.; Wang, Y. F.; Wong, C. H. J. Am. Chem. Soc. 1989, 111, 3924;
29. (o) Ziegler, T.; Straub, A.; Effenberger, F. Angew. Chem., Int. Ed. Engl. 1988, 27, 716;
30. (p) Fleet, G. W. J.; Smith, P. W. Tetrahedron 1986, 42, 5685.
31. For the syntheses of D-fagomine 2, see: (a) Bartali, L.; Casini, A.; Guarana, A.; Occhiato, E. G.; Scarpi, D. Eur. J. Org. Chem. 2010, 5831;
32. (b) Bartali, L.; Scarpi, D.; Guarna, A.; Prandi, C.; Occhiato, E. G. Synlett 2009, 913;
33. (c) Kumari, N.; Reddy, B. G.; Vankar, Y. D. Eur. J. Org. Chem. 2009, 160;
34. (d) Yokoyama, H.; Ejiri, H.; Miyazawa, M.; Yamaguchi, S.; Hirai, Y. Tetrahedron: Asymmetry 2007, 18, 852;
35. (e) Castillo, J. A.; Calveras, J.; Casas, J.; Mitjans, M.; Vinardell, M. P.; Parella, T.; Inoue, T.; Sprenger, G. A.; Joglar, J.; Clapés, P. Org. Lett. 2006, 8, 6067;
36. (f) Takahata, H.; Banba, Y.; Ouchi, H.; Nemoto, H.; Kato, A.; Adachi, I. J. Org. Chem. 2003, 68, 3603;
37. (g) Lindsay, K. B.; Pyne, S. G. J. Org. Chem. 2002, 67, 7774;
38. (h) Désiré, J.; Dransfield, P. J.; Gore, P. M.; Shipman, M. Synlett 2001, 1329;
39. (i) Banba, Y.; Abe, C.; Nemoto, H.; Kato, A.; Adachi, I.,; Takahata, H. Tetrahedron: Asymmetry 2001, 12, 817;
40. (j) Degiorgis, F.; Lombardo, M.; Trombini, C. Synthesis 1997, 1243;
41. (k) Fleet, G. W. J.; Smith, P. W. Tetrahedron Lett. 1985, 26, 1469.
42. Pham, V. T.; Joo, J. E.; Lee, K. Y.; Kim, T.W.; Mu, Y.; Ham,W. H. Tetrahedron 2010, 66, 2123.
43. (a) Joo, J. E.; Pham, V. T.; Tian, Y. S.; Chung, Y. S.; Lee, K. Y.; Ham, W. H. Org. Biomol. Chem. 2008, 6, 1498;
44. (b) Joo, J. E.; Lee, K. Y.; Pham, V. T.; Ham, W. H. Eur. J. Org. Chem. 2007, 1586;
45. (c) Joo, J. E.; Lee, K. Y.; Pham, V. T.; Tian, Y. S.; Ham, W. H. Org. Lett. 2007, 9, 3627.
46. 6) of compound 3d has the similar value 4.0 Hz, compared to all anti,syn-oxazines previously reported.