Selective methylphosphonylation of an echinocandin B analog derived from LY303366

Tetrahedron

Volumn 59, Issue 15, 2003, Pages 2667-2672

  Udodong, Uko E ^a   Hansen, Marvin M ^a   Verral, Daniel E ^a   Harkness, Allen R ^a   Grutsch, John L ^a   Miller, William D ^a   Astleford, Bret ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

Echinocandin B; LY303366; Methylphosphonylation

Indexed keywords

ANIDULAFUNGIN; BIS[(4 BROMOPHENYL)METHYL]DIMETHYLDIPHOSPHONATE; ECHINOCANDIN B DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DECOMPOSITION; DEPROTECTION REACTION; HYDROLYSIS; PRIORITY JOURNAL;

EID: 0037424823     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00310-7     Document Type: Article

References (30)

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13. See, for example: (a) Campbell D.A., Bermak J.C. J. Org. Chem. 59:1994;658 (b) Saady M., Lebeau L., Mioskowski C. Tetrahedron Lett. 36:1995;2239 (c) Willems H.A.M., Veenemen G.H., Westerduin P. Tetrahedron Lett. 33:1992;2075 (d) Valentijn A.R.P.M., van der Marel G.A., Cohen L.H., van Boom J.H. Synlett. 1991;663 (e) Tawfik D.S., Eshhar Z., Bentolila A., Green B.S. Synthesis. 1993;968 (f) Saady M., Lebeau L., Mioskowski C. Tetrahedron Lett. 36:1995;4785 (g) Wozniak L.A., Wieczorek M., Pyzowski J., Majzner W., Stec W.J. J. Org. Chem. 63:1998;5395 (h) Wozniak L.A., Chworos A., Pyzowski J., Stec W.J. J. Org. Chem. 63:1998;9109 (i) Lesnikowski Z.J., Zabawaska D., Jaworska-Maslanka M.M., Schinazi R.F., Stec W.J. New J. Chem. 18:1994;1197.
14. See, for example: (a) Campbell D.A., Bermak J.C. J. Org. Chem. 59:1994;658 (b) Saady M., Lebeau L., Mioskowski C. Tetrahedron Lett. 36:1995;2239 (c) Willems H.A.M., Veenemen G.H., Westerduin P. Tetrahedron Lett. 33:1992;2075 (d) Valentijn A.R.P.M., van der Marel G.A., Cohen L.H., van Boom J.H. Synlett. 1991;663 (e) Tawfik D.S., Eshhar Z., Bentolila A., Green B.S. Synthesis. 1993;968 (f) Saady M., Lebeau L., Mioskowski C. Tetrahedron Lett. 36:1995;4785 (g) Wozniak L.A., Wieczorek M., Pyzowski J., Majzner W., Stec W.J. J. Org. Chem. 63:1998;5395 (h) Wozniak L.A., Chworos A., Pyzowski J., Stec W.J. J. Org. Chem. 63:1998;9109 (i) Lesnikowski Z.J., Zabawaska D., Jaworska-Maslanka M.M., Schinazi R.F., Stec W.J. New J. Chem. 18:1994;1197.
15. See, for example: (a) Campbell D.A., Bermak J.C. J. Org. Chem. 59:1994;658 (b) Saady M., Lebeau L., Mioskowski C. Tetrahedron Lett. 36:1995;2239 (c) Willems H.A.M., Veenemen G.H., Westerduin P. Tetrahedron Lett. 33:1992;2075 (d) Valentijn A.R.P.M., van der Marel G.A., Cohen L.H., van Boom J.H. Synlett. 1991;663 (e) Tawfik D.S., Eshhar Z., Bentolila A., Green B.S. Synthesis. 1993;968 (f) Saady M., Lebeau L., Mioskowski C. Tetrahedron Lett. 36:1995;4785 (g) Wozniak L.A., Wieczorek M., Pyzowski J., Majzner W., Stec W.J. J. Org. Chem. 63:1998;5395 (h) Wozniak L.A., Chworos A., Pyzowski J., Stec W.J. J. Org. Chem. 63:1998;9109 (i) Lesnikowski Z.J., Zabawaska D., Jaworska-Maslanka M.M., Schinazi R.F., Stec W.J. New J. Chem. 18:1994;1197.
16. See, for example: (a) Campbell D.A., Bermak J.C. J. Org. Chem. 59:1994;658 (b) Saady M., Lebeau L., Mioskowski C. Tetrahedron Lett. 36:1995;2239 (c) Willems H.A.M., Veenemen G.H., Westerduin P. Tetrahedron Lett. 33:1992;2075 (d) Valentijn A.R.P.M., van der Marel G.A., Cohen L.H., van Boom J.H. Synlett. 1991;663 (e) Tawfik D.S., Eshhar Z., Bentolila A., Green B.S. Synthesis. 1993;968 (f) Saady M., Lebeau L., Mioskowski C. Tetrahedron Lett. 36:1995;4785 (g) Wozniak L.A., Wieczorek M., Pyzowski J., Majzner W., Stec W.J. J. Org. Chem. 63:1998;5395 (h) Wozniak L.A., Chworos A., Pyzowski J., Stec W.J. J. Org. Chem. 63:1998;9109 (i) Lesnikowski Z.J., Zabawaska D., Jaworska-Maslanka M.M., Schinazi R.F., Stec W.J. New J. Chem. 18:1994;1197.
17. See, for example: (a) Campbell D.A., Bermak J.C. J. Org. Chem. 59:1994;658 (b) Saady M., Lebeau L., Mioskowski C. Tetrahedron Lett. 36:1995;2239 (c) Willems H.A.M., Veenemen G.H., Westerduin P. Tetrahedron Lett. 33:1992;2075 (d) Valentijn A.R.P.M., van der Marel G.A., Cohen L.H., van Boom J.H. Synlett. 1991;663 (e) Tawfik D.S., Eshhar Z., Bentolila A., Green B.S. Synthesis. 1993;968 (f) Saady M., Lebeau L., Mioskowski C. Tetrahedron Lett. 36:1995;4785 (g) Wozniak L.A., Wieczorek M., Pyzowski J., Majzner W., Stec W.J. J. Org. Chem. 63:1998;5395 (h) Wozniak L.A., Chworos A., Pyzowski J., Stec W.J. J. Org. Chem. 63:1998;9109 (i) Lesnikowski Z.J., Zabawaska D., Jaworska-Maslanka M.M., Schinazi R.F., Stec W.J. New J. Chem. 18:1994;1197.
18. See, for example: (a) Campbell D.A., Bermak J.C. J. Org. Chem. 59:1994;658 (b) Saady M., Lebeau L., Mioskowski C. Tetrahedron Lett. 36:1995;2239 (c) Willems H.A.M., Veenemen G.H., Westerduin P. Tetrahedron Lett. 33:1992;2075 (d) Valentijn A.R.P.M., van der Marel G.A., Cohen L.H., van Boom J.H. Synlett. 1991;663 (e) Tawfik D.S., Eshhar Z., Bentolila A., Green B.S. Synthesis. 1993;968 (f) Saady M., Lebeau L., Mioskowski C. Tetrahedron Lett. 36:1995;4785 (g) Wozniak L.A., Wieczorek M., Pyzowski J., Majzner W., Stec W.J. J. Org. Chem. 63:1998;5395 (h) Wozniak L.A., Chworos A., Pyzowski J., Stec W.J. J. Org. Chem. 63:1998;9109 (i) Lesnikowski Z.J., Zabawaska D., Jaworska-Maslanka M.M., Schinazi R.F., Stec W.J. New J. Chem. 18:1994;1197.
19. See, for example: (a) Campbell D.A., Bermak J.C. J. Org. Chem. 59:1994;658 (b) Saady M., Lebeau L., Mioskowski C. Tetrahedron Lett. 36:1995;2239 (c) Willems H.A.M., Veenemen G.H., Westerduin P. Tetrahedron Lett. 33:1992;2075 (d) Valentijn A.R.P.M., van der Marel G.A., Cohen L.H., van Boom J.H. Synlett. 1991;663 (e) Tawfik D.S., Eshhar Z., Bentolila A., Green B.S. Synthesis. 1993;968 (f) Saady M., Lebeau L., Mioskowski C. Tetrahedron Lett. 36:1995;4785 (g) Wozniak L.A., Wieczorek M., Pyzowski J., Majzner W., Stec W.J. J. Org. Chem. 63:1998;5395 (h) Wozniak L.A., Chworos A., Pyzowski J., Stec W.J. J. Org. Chem. 63:1998;9109 (i) Lesnikowski Z.J., Zabawaska D., Jaworska-Maslanka M.M., Schinazi R.F., Stec W.J. New J. Chem. 18:1994;1197.
20. See, for example: (a) Campbell D.A., Bermak J.C. J. Org. Chem. 59:1994;658 (b) Saady M., Lebeau L., Mioskowski C. Tetrahedron Lett. 36:1995;2239 (c) Willems H.A.M., Veenemen G.H., Westerduin P. Tetrahedron Lett. 33:1992;2075 (d) Valentijn A.R.P.M., van der Marel G.A., Cohen L.H., van Boom J.H. Synlett. 1991;663 (e) Tawfik D.S., Eshhar Z., Bentolila A., Green B.S. Synthesis. 1993;968 (f) Saady M., Lebeau L., Mioskowski C. Tetrahedron Lett. 36:1995;4785 (g) Wozniak L.A., Wieczorek M., Pyzowski J., Majzner W., Stec W.J. J. Org. Chem. 63:1998;5395 (h) Wozniak L.A., Chworos A., Pyzowski J., Stec W.J. J. Org. Chem. 63:1998;9109 (i) Lesnikowski Z.J., Zabawaska D., Jaworska-Maslanka M.M., Schinazi R.F., Stec W.J. New J. Chem. 18:1994;1197.
21. Compound 8 is only observed by HPLC as monoester 6 following an aqueous quench. Selective formation of the desired phosphonate monoester has been reported using phenylphosphonic dichloride. With alkyl phosphonic dichlorides, variable success has been reported. See: (a) Zhao K., Landry D.W. Tetrahedron. 49:1993;363. Entries 8 and 9 in Table 1
22. (b) Yang G., Zhao K., Landy D.W. Tetrahedron Lett. 39:1998;2449. Entries 3 and 4 in Table 1
23. (c) Mlodnosky K.L., Holmes H.M., Lam V.Q., Berkman C.E. Tetrahedron Lett. 38:1997;8803.
24. Conversion of phosphonic chlorides to the diphosphonate with water is known. In our process, this results in a mixture of diphosphonate 7, diester 4 and phosphonate monoester 6. Due to instability of 7, this mixture cannot be purified. See: Ohms G., Grossmann G., Schwab B., Schiefer H. Phosphorus Sulfur Silicon Relat. Elem. 68:1992;77.
25. The process in path b is a significant improvement over path a and avoids the formation of 4-bromobenzyl iodide, a strong lachrymator. See: Zervas L., Kilaris I. J. Am. Chem. Soc. 77:1955;5354.
26. Khorana H.G., Todd A.R. J. Am. Chem. Soc. 1953;2257.
27. Diphosphonate 7 is stable to storage in a freezer for at least four months.
28. +. See Ref. 4.
29. 31P NMR spectroscopy.
30. Although toxicity data for the phosphorus compounds described here is not available, the toxicity of related esters have been recognized. Hence, all phosphorus esters should be handled with caution O'Brien R.D. Toxic Phosphorus Esters. Chemistry, Metabolism, and Biological Effects. 1960;Academic, London. See, for example, tetraethyl diphosphate in The Merck Index; 11th ed., 1989, p 1450.