Short synthesis of both enantiomers of cytoxazone using the Petasis reaction

Tetrahedron Asymmetry

Volumn 15, Issue 19, 2004, Pages 3149-3153

  Sugiyama, Shigeo ^a   Arai, Satoshi ^a   Ishii, Keitaro ^a  

^a MEIJI PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; ETHYLAMINE; GLYCERALDEHYDE; HYDROXYMETHYL(4 METHOXYPHENYL)OXAZOLIDIN 2 ONE; OXAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DESILYLATION; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS; SILYLATION;

EID: 5344267398     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2004.08.004     Document Type: Article

References (29)

1. H. Kakeya, M. Morishita, K. Kobinata, M. Osono, M. Ishizuka, and H. Osada J. Antibiot. 51 1998 1126 1128
2. H. Kakeya, M. Morishita, H. Koshino, T.-i Morita, K. Kobayashi, and H. Osada J. Org. Chem. 64 1999 1052 1053
3. O. Miyata, H. Asai, and T. Naito Synlett 1999 1915 1916
4. O. Miyata, T. Koizumi, H. Asai, R. Iba, and T. Naito Tetrahedron 60 2004 3893 3914
5. Z. Hamersak, E. Ljubovic, M. Mercep, M. Mesic, and V. Sunjic Synthesis 2001 1989 1992
6. Y. Sakamoto, A. Shiraishi, J. Seonhee, and T. Nakata Tetrahedron Lett. 40 1999 4203 4206
7. M. Seki, and K. Mori Eur. J. Org. Chem. 1999 2965 2967
8. J.N. Park, S.Y. Ko, and H.Y. Koh Tetrahedron Lett. 41 2000 5553 5556
9. A. Madhan, A.R. Kumar, and B.V. Rao Tetrahedron: Asymmetry 12 2001 2009 2011
10. M. Carda, F. Gonzalez, R. Sanchez, and J.A. Marco Tetrahedron: Asymmetry 13 2002 1005 1010
11. P.H. Carter, J.R. LaPorte, P.A. Scherle, and C.P. Decicco Bioorg. Med. Chem. Lett. 13 2003 1237 1239
12. A.R. Kumar, G. Bhaskar, A. Madhan, and B.V. Rao Synth. Commun. 33 2003 2003 2907
13. S. Milicevic, R. Matovic, and R.N. Saicic Tetrahedron Lett. 45 2004 955 957
14. S.G. Davies, D.G. Hughes, R.L. Nicholson, A.D. Smith, and A.J. Wright Org. Biomol. Chem. 2 2004 1549 1553
15. Petasis, N. A. Method for the synthesis of amines and amino acids with organoboran derivatives. PCT/US97/11161, June 27, 1997
16. N.A. Petasis, and I.A. Zavialov J. Am. Chem. Soc. 119 1997 445 446
17. N.A. Petasis, and I.A. Zavialov J. Am. Chem. Soc. 129 1998 11798 11799
18. S. Sugiyama, K. Morishita, and K. Ishii Heterocycles 55 2001 353 364
19. S. Sugiyama, K. Morishita, M. Chiba, and K. Ishii Heterocycles 57 2002 637 648
20. G. Cardillo, M. Orena, S. Sandri, and C. Tomasini Tetrahedron 43 1987 2505 2512
21. S. Tanimori, U. Inaba, Y. Kato, and M. Kirihara Tetrahedron 59 2003 3745 3751
22. S. Tanimori, and M. Kirihara Tetrahedron Lett. 41 2000 6785 6788
23. S. Sugiyama, S. Watanabe, and K. Ishii Tetrahedron Lett. 40 1999 7489 7492
24. S. Sugiyama, S. Watanabe, T. Inoue, R. Kurihara, T. Itou, and K. Ishii Tetrahedron 59 2003 3417 3425
25. S. Sugiyama, T. Inoue, and K. Ishii Tetrahedron: Asymmetry 14 2003 2153 2160
26. A recent example, see E. Marcantori, T. Mecozzi, and M. Petrini J. Org. Chem. 67 2002 2989 2994
27. A recent example, see H. Xiong, R.P. Hsung, C.R. Berry, and C. Rameshkumar J. Am. Chem. Soc. 123 2001 7174 7175
28. M. Noji, T. Ohno, K. Fuji, N. Futaba, H. Tajima, and K. Ishii J. Org. Chem. 68 2003 9340 9347
29. N.A. Petasis, A. Goodman, and I.A. Zavialov Tetrahedron 53 1997 16463 16470