The sulfinyl moiety as an internal nucleophile. Part 8: Efficient, stereospecific synthesis of (+)-polyoxamic acid

Tetrahedron Letters

Volumn 44, Issue 35, 2003, Pages 6713-6715

  Raghavan, Sadagopan ^a   Joseph, Suju C ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

(+) polyoxamic acid; Bromohydrin; Stereospecific; Sulfinyl group

Indexed keywords

OXAMIC ACID; POLYOXAMIC ACID; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; HYDROLYSIS; HYDROXYLATION; MOLECULAR INTERACTION; REDUCTION; STEREOSPECIFICITY;

EID: 0043172237     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01650-2     Document Type: Article

References (39)

1. Isono K., Suzuki S. Heterocycles. 13:1979;333.
2. Isono K., Asahi K., Suzuki S. J. Am. Chem. Soc. 91:1969;7490.
3. Mori M., Kakiki K., Misato T. Agric. Biol. Chem. 38:1974;699.
4. Shenbagamurthi P., Smith H.A., Becker J.M., Steinfeld A., Naider F. J. Med. Chem. 26:1983;1518.
5. Davis F.A., Prasad K.R., Carrol P.J. J. Org. Chem. 67:2002;7802.
6. Kim K.S., Lee Y.J., Kim J.H., Sung D.K. J. Chem. Soc., Chem. Commun. 2002;1116.
7. Dehoux C., Monthieu C., Baltas M., Gorrichon L. Synthesis. 2000;1409.
8. Savage I., Thomas E.J., Wilson P.D. J. Chem. Soc., Perkin Trans. 1. 1999;3291.
9. Ghosh A.K., Wang Y. Tetrahedron. 55:1999;13369.
10. Uchida K., Kato K., Akita H. Synthesis. 1999;1541.
11. Harwood L.M., Robertson S.M. J. Chem. Soc., Chem. Commun. 1998;2641.
12. Kang S.H., Choi H.-W. J. Chem. Soc., Chem. Commun. 1996;1521.
13. Trost B.M., Krueger A.C., Bunt R.C., Zambrano J. J. Am. Chem. Soc. 118:1996;6520.
14. Jackson R.F.W., Palmer N.J., Wythes M.J., Clegg W., Elsegood M.R.J. J. Org. Chem. 60:1995;6431.
15. Matsuura F., Hamada Y., Shiori T. Tetrahedron Lett. 35:1994;733.
16. Marshall J.A., Seletsky B.M., Coan P.S. J. Org. Chem. 59:1994;5139.
17. Chida N., Koizumi K., Kitada Y., Yokoyama C., Ogawa S. J. Chem. Soc., Chem. Commun. 1994;111.
18. Paz M.M., Sardina F.J. J. Org. Chem. 58:1993;6990.
19. Banik B.K., Manhas M.S., Bose A.K. J. Org. Chem. 58:1993;307.
20. Dondoni A., Franco S., Merchan F.L., Merino P., Tejero T. Tetrahedron Lett. 34:1993;5479.
21. Dureault A., Carreaux F., Depezay J.C. Synthesis. 1991;150.
22. Mukaiyama T., Suzuki K., Yamada T., Tabusa F. Tetrahedron. 46:1990;265.
23. Ikota N. Chem. Pharm. Bull. Jpn. 37:1989;3399.
24. Garner P., Park J.M. J. Org. Chem. 53:1988;2979.
25. Saksena A.K., Lovey R.G., Girijavallabhan V.M., Ganguly A.K. J. Org. Chem. 51:1986;5024.
26. Kuzuhara H., Emoto S. Tetrahedron Lett. 1973;5051.
27. Raghavan S., Ramakrishna Reddy S., Tony K.A., Naveen Kumar Ch., Varma A.K., Nangia A. J. Org. Chem. 67:2002;5838.
28. Raghavan S., Rasheed M.A., Joseph S.C., Rajender A. J. Chem. Soc., Chem. Commun. 1999;1845.
29. Solladie G., Frechou C., Hutt G., Demailly G. Bull. Soc. Chim. Fr. 1987;827.
30. Solladie G., Demailly G., Greck C. Tetrahedron Lett. 26:1985;435.
31. Solladie G., Frechou C., Demailly G., Greck C. J. Org. Chem. 51:1986;1912.
32. Carreno M.C., Garcia Ruano J.L., Martin A.M., Pedregal C., Rodriguez J.H., Rubio A., Sanchez J., Solladie G. J. Org. Chem. 55:1990;2120.
33. Dana G., Danechpajouh H. Bull. Soc. Chim. Fr. 1980;395.
34. Chamberlin A.R., Mulholland R.L. Jr., Kahn S.D., Hehre W.J. J. Am. Chem. Soc. 109:1987;672.
35. Khuddus M.A., Swern D. J. Am. Chem. Soc. 95:1973;8393.
36. Pummerer R. Chem. Ber. 42:1909;2282.
37. Sugihara H., Tanikaga R., Kaji A. Synthesis. 1978;881.
38. Padwa A., Gunn D.E. Jr., Osterhout M.H. Synthesis. 1997;1353.
39. De Nooy A.E.J., Besemer A.C., van Bekkum H. Synthesis. 1996;1153.