The synthesis and evaluation of a solution phase indexed combinatorial library of non-natural polyenes for reversal of p-glycoprotein mediated multidrug resistance

Journal of Organic Chemistry

Volumn 65, Issue 16, 2000, Pages 4973-4983

  Andrus, Merritt B ^a   Turner, Timothy M ^a   Sauna, Zuben E ^b   Ambudkar, Suresh V ^b  

^a Brigham Young University   (United States)

^b NATIONAL CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; ADENOSINE TRIPHOSPHATASE; AMIDE; BORANE DERIVATIVE; BORON; CINCHONINE; DOXORUBICIN; GLYCOPROTEIN P; IODIDE; METHYL GROUP; NAPHTHYL GROUP; NOREPHEDRINE; PALLADIUM; POLYENE; PROPIONIC ACID;

ANIMAL CELL; ARTICLE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; INSECT; MULTIDRUG RESISTANCE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STOICHIOMETRY; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

ADENOSINE TRIPHOSPHATASES; ANTINEOPLASTIC AGENTS; COMBINATORIAL CHEMISTRY TECHNIQUES; DOXORUBICIN; DRUG RESISTANCE, MULTIPLE; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; P-GLYCOPROTEIN; POLYENES; QUINOLINES; SOLUTIONS; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

EID: 0034637475     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000453m     Document Type: Article

References (63)

1. Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555.
2. Lam, K. S.; Salmon, S. E.; Hersh, E. M.; Hruby, V. J.; Kazmierski, W. M.; Knapp, R. J. Nature 1991, 354, 82.
3. Pirrung, M. C.; Chen, J. J. Am. Chem. Soc. 1995, 117, 1240.
4. Carell, T.; Wintner, E. A.; Rebek, J. Jr. Angew. Chem., Int. Ed. Engl. 1994, 33, 2061. Boger, D. L.; Chai, W.; Ozer, R. S.; Anderson, C. Bioorg. Med. Chem. Lett. 1997, 7, 463.
5. Carell, T.; Wintner, E. A.; Rebek, J. Jr. Angew. Chem., Int. Ed. Engl. 1994, 33, 2061. Boger, D. L.; Chai, W.; Ozer, R. S.; Anderson, C. Bioorg. Med. Chem. Lett. 1997, 7, 463.
6. Nicolaou, K. C.; Pastor, J.; Winssinger, N.; Murphy, F. J. Am. Chem. Soc. 1998, 120, 5132. Tan, D. S.; Foley, M. A.; Shair, M. D.; Schreiber, S. L. J. Am. Chem. Soc. 1998, 120, 8565.
7. Nicolaou, K. C.; Pastor, J.; Winssinger, N.; Murphy, F. J. Am. Chem. Soc. 1998, 120, 5132. Tan, D. S.; Foley, M. A.; Shair, M. D.; Schreiber, S. L. J. Am. Chem. Soc. 1998, 120, 8565.
8. Andrus, M. B.; Turner, T. M.; Asgari, D.; Wenke, L. J. Org. Chem. 1999, 64, 2978.
9. (a) Andrus, M. B.; Lepore, S. D. J. Am. Chem. Soc. 1997, 119, 2327.
10. (b) Andrus, M. B.; Lepore, S. D.; Turner, T. M. J. Am. Chem. Soc. 1997, 119, 12159.
11. Kim, Y. J.; Furihata, K.; Yamanaka, S.; Fudo, R.; Seto, H. J. Antibiot. 1991, 44, 553.
12. Ambudkar, S. V.; Dey, S.; Hrycyna, C. A.; Ramachandra, M. Pastan, I.; Gottesman, M. M. Annu. Rev. Pharmacol. Toxicol. 1999, 39, 361-398. Gottesman, M. M.; Pastan, I. Annu. Rev. Biochem. 1993, 62, 385-427.
13. Ambudkar, S. V.; Dey, S.; Hrycyna, C. A.; Ramachandra, M. Pastan, I.; Gottesman, M. M. Annu. Rev. Pharmacol. Toxicol. 1999, 39, 361-398. Gottesman, M. M.; Pastan, I. Annu. Rev. Biochem. 1993, 62, 385-427.
14. Ambudkar, S. V. Methods Enzymol. 1998, 292, 504-514. Dey, S.; Ramachandra, M.; Pastan, I.; Gottesman, M. M.; Ambudkar, S. V. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 10594.
15. Ambudkar, S. V. Methods Enzymol. 1998, 292, 504-514. Dey, S.; Ramachandra, M.; Pastan, I.; Gottesman, M. M.; Ambudkar, S. V. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 10594.
16. Germann, U. A. Eur. J. Can. 1996, 32A, 927. Greenberger, L. M. J. Biol. Chem. 1993, 268, 11417.
17. Germann, U. A. Eur. J. Can. 1996, 32A, 927. Greenberger, L. M. J. Biol. Chem. 1993, 268, 11417.
18. (a) Loo, T. W.; Clarke, D. M. J. Biol. Chem. 1993, 268, 19965
19. (b) Loo, T. W.; Clarke, D. M. J. Biol. Chem. 1995, 270, 21839.
20. Recently, a low resolution electron diffraction structure of Pgp (25 Å) was reported: (a) Rosenburg, M. F.; Callaghan, R.; Ford, R. C.; Higgins, C F. J. Biol. Chem. 1997, 272, 10685
21. (b) Higgins, C. F.; Callaghan, R. Semin. Can. Biol. 1997, 8, 135.
22. (a) Carell, T.; Wintner, E. A.; Bashir-Hashemi, A.; Rebek J. Angew. Chem., Int. Ed. Engl. 1994, 33, 2059
23. (b) Carell, T.; Wintner, E. A.; Sutherland, A. J.; Rebek, J.; Dunayevskiy, Y. M.; Vouros, P. Chemistry & Biology 1995, 2, 171.
24. (a) Smith, P. W.; Lai, J. Y. Q.; Whittington, A. R.; Cox, B.; Houston, J. G. Bioorg. Med. Chem. Lett. 1994, 4, 2821
25. (b) Pirrung, M. C.; Chen, J. J. Am. Chem. Soc. 1995, 117, 1240
26. Pirrung, M. C.; Chau, J. H-L.; Chen, J. Chemistry & Biology 1995, 2, 621. For other recent examples of solution phase libraries
27. Déprez, B.; Williard, X.; Bourel, L.; Coste, H.; Hyafil, F.; Tartar, A. J. Am. Chem. Soc. 1995, 117, 5405
28. (e) Han, H.; Wolfe, M. M.; Brenner, S.; Janda, K. D. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 6419
29. (f) Edge, C. J.; Rademacher, T. W.; Wormald, M. R.; Parekh, R. B.; Butters, T. D.; Wing, D. R.; Dwek, R. A. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 6338
30. (g) Boger, D. L. Chai, W.; Jin, Q. J. Am. Chem. Soc. 1998, 120, 7220
31. (h) An example of a C-C bond forming library was recently reported although no biological evaluation was mention: Boger, D. L.; Goldberg, J.; Andersson, C.-M. J. Org. Chem. 1999, 64, 2422.
32. 3) followed by DIBAL reduction afforded the desired aldehyde.
33. Alternatively, aldehydes 7a-f were converted to the unsaturated esters, reduced to the allyl alcohol, and oxidized to the enals 8a-f with TPAP. Griffith, W. P.; Ley, S. V. Aldrichim. Acta 1990, 23, 13.
34. Brown, H. C.; Bhat, K. S. J. Am. Chem. Soc. 1986, 108, 293.
35. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
36. Andrus, M. B.; Lepore, S. D.; Sclafani, J. A. Tetrahedron Lett. 1997, 38, 4043.
37. Takai, K.; Nitta, K.; Utimoto, K. J. Am. Chem. Soc. 1986, 108, 7408.
38. Crotylboron tartrates were also considered: Roush, W. R.; Ando, K.; Powers, D. B.; Palkowitz, A. D.; Halterman, R. L. J. Am. Chem. Soc. 1990, 112, 6339 and references therein. Aldol routes include: Fleming, I. In Comprehensive Organic Synthesis, Vol. 2; Heathcock, C. H., Ed.; Pergamon Press: Oxford, 1991; p 563. Also see: Myers, A. G.; Widdowson, K. L J. Am. Chem. Soc. 1990, 112, 9672. Walker, M. A.; Heathcock, C. H. J. Org. Chem. 1991, 56, 5747. Van Draanen, N. A.; Arseniyadis, S.; Crimmins, M. T.; Heathcock, C. H. J. Org. Chem. 1991, 56, 2499. Braun, M.; Sacha, H.; Angew. Chem., Int. Ed. Engl. 1991, 30, 1318. Gennari, C.; Hewkin, C. T.; Molinari, F.; Bernardi, A.; Comotti, A.; Goodman, J. M.; Paterson, I. J. Org. Chem. 1992, 57, 5173. Gennari, C.; Moresca, D.; Vieth, S.; Vulpetti, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1618. Oppolzer, W.; Lienard, P. Tetrahedron Lett. 1993, 34, 4321. Paterson, I.; Wallace, D. J.; Velazquez, S. M. Tetrahedron Lett. 1994, 35, 9083. Wang, Y.-C.; Hung, A.-W.; Chang, C. -S.; Van, T.-H.; J. Org. Chem. 1996, 61, 2038. Ghosh, A. K.; Ohnishi, M. J. Am. Chem. Soc. 1996, 118, 2527. Ghosh, A. K.; Fidanze, S.; Onishi, M.; Hussain, K. A. Tetrahedron Lett. 1997, 38, 7171. Li, Z.; Wu, R.; Michalczyk, R.; Dunlap, R. B.; Odom, J. D.; Silks, L. A. III J. Am. Chem. Soc. 2000, 122, 386.
39. Crotylboron tartrates were also considered: Roush, W. R.; Ando, K.; Powers, D. B.; Palkowitz, A. D.; Halterman, R. L. J. Am. Chem. Soc. 1990, 112, 6339 and references therein. Aldol routes include: Fleming, I. In Comprehensive Organic Synthesis, Vol. 2; Heathcock, C. H., Ed.; Pergamon Press: Oxford, 1991; p 563. Also see: Myers, A. G.; Widdowson, K. L J. Am. Chem. Soc. 1990, 112, 9672. Walker, M. A.; Heathcock, C. H. J. Org. Chem. 1991, 56, 5747. Van Draanen, N. A.; Arseniyadis, S.; Crimmins, M. T.; Heathcock, C. H. J. Org. Chem. 1991, 56, 2499. Braun, M.; Sacha, H.; Angew. Chem., Int. Ed. Engl. 1991, 30, 1318. Gennari, C.; Hewkin, C. T.; Molinari, F.; Bernardi, A.; Comotti, A.; Goodman, J. M.; Paterson, I. J. Org. Chem. 1992, 57, 5173. Gennari, C.; Moresca, D.; Vieth, S.; Vulpetti, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1618. Oppolzer, W.; Lienard, P. Tetrahedron Lett. 1993, 34, 4321. Paterson, I.; Wallace, D. J.; Velazquez, S. M. Tetrahedron Lett. 1994, 35, 9083. Wang, Y.-C.; Hung, A.-W.; Chang, C. -S.; Van, T.-H.; J. Org. Chem. 1996, 61, 2038. Ghosh, A. K.; Ohnishi, M. J. Am. Chem. Soc. 1996, 118, 2527. Ghosh, A. K.; Fidanze, S.; Onishi, M.; Hussain, K. A. Tetrahedron Lett. 1997, 38, 7171. Li, Z.; Wu, R.; Michalczyk, R.; Dunlap, R. B.; Odom, J. D.; Silks, L. A. III J. Am. Chem. Soc. 2000, 122, 386.
40. Crotylboron tartrates were also considered: Roush, W. R.; Ando, K.; Powers, D. B.; Palkowitz, A. D.; Halterman, R. L. J. Am. Chem. Soc. 1990, 112, 6339 and references therein. Aldol routes include: Fleming, I. In Comprehensive Organic Synthesis, Vol. 2; Heathcock, C. H., Ed.; Pergamon Press: Oxford, 1991; p 563. Also see: Myers, A. G.; Widdowson, K. L J. Am. Chem. Soc. 1990, 112, 9672. Walker, M. A.; Heathcock, C. H. J. Org. Chem. 1991, 56, 5747. Van Draanen, N. A.; Arseniyadis, S.; Crimmins, M. T.; Heathcock, C. H. J. Org. Chem. 1991, 56, 2499. Braun, M.; Sacha, H.; Angew. Chem., Int. Ed. Engl. 1991, 30, 1318. Gennari, C.; Hewkin, C. T.; Molinari, F.; Bernardi, A.; Comotti, A.; Goodman, J. M.; Paterson, I. J. Org. Chem. 1992, 57, 5173. Gennari, C.; Moresca, D.; Vieth, S.; Vulpetti, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1618. Oppolzer, W.; Lienard, P. Tetrahedron Lett. 1993, 34, 4321. Paterson, I.; Wallace, D. J.; Velazquez, S. M. Tetrahedron Lett. 1994, 35, 9083. Wang, Y.-C.; Hung, A.-W.; Chang, C. -S.; Van, T.-H.; J. Org. Chem. 1996, 61, 2038. Ghosh, A. K.; Ohnishi, M. J. Am. Chem. Soc. 1996, 118, 2527. Ghosh, A. K.; Fidanze, S.; Onishi, M.; Hussain, K. A. Tetrahedron Lett. 1997, 38, 7171. Li, Z.; Wu, R.; Michalczyk, R.; Dunlap, R. B.; Odom, J. D.; Silks, L. A. III J. Am. Chem. Soc. 2000, 122, 386.
41. Crotylboron tartrates were also considered: Roush, W. R.; Ando, K.; Powers, D. B.; Palkowitz, A. D.; Halterman, R. L. J. Am. Chem. Soc. 1990, 112, 6339 and references therein. Aldol routes include: Fleming, I. In Comprehensive Organic Synthesis, Vol. 2; Heathcock, C. H., Ed.; Pergamon Press: Oxford, 1991; p 563. Also see: Myers, A. G.; Widdowson, K. L J. Am. Chem. Soc. 1990, 112, 9672. Walker, M. A.; Heathcock, C. H. J. Org. Chem. 1991, 56, 5747. Van Draanen, N. A.; Arseniyadis, S.; Crimmins, M. T.; Heathcock, C. H. J. Org. Chem. 1991, 56, 2499. Braun, M.; Sacha, H.; Angew. Chem., Int. Ed. Engl. 1991, 30, 1318. Gennari, C.; Hewkin, C. T.; Molinari, F.; Bernardi, A.; Comotti, A.; Goodman, J. M.; Paterson, I. J. Org. Chem. 1992, 57, 5173. Gennari, C.; Moresca, D.; Vieth, S.; Vulpetti, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1618. Oppolzer, W.; Lienard, P. Tetrahedron Lett. 1993, 34, 4321. Paterson, I.; Wallace, D. J.; Velazquez, S. M. Tetrahedron Lett. 1994, 35, 9083. Wang, Y.-C.; Hung, A.-W.; Chang, C. -S.; Van, T.-H.; J. Org. Chem. 1996, 61, 2038. Ghosh, A. K.; Ohnishi, M. J. Am. Chem. Soc. 1996, 118, 2527. Ghosh, A. K.; Fidanze, S.; Onishi, M.; Hussain, K. A. Tetrahedron Lett. 1997, 38, 7171. Li, Z.; Wu, R.; Michalczyk, R.; Dunlap, R. B.; Odom, J. D.; Silks, L. A. III J. Am. Chem. Soc. 2000, 122, 386.
42. Crotylboron tartrates were also considered: Roush, W. R.; Ando, K.; Powers, D. B.; Palkowitz, A. D.; Halterman, R. L. J. Am. Chem. Soc. 1990, 112, 6339 and references therein. Aldol routes include: Fleming, I. In Comprehensive Organic Synthesis, Vol. 2; Heathcock, C. H., Ed.; Pergamon Press: Oxford, 1991; p 563. Also see: Myers, A. G.; Widdowson, K. L J. Am. Chem. Soc. 1990, 112, 9672. Walker, M. A.; Heathcock, C. H. J. Org. Chem. 1991, 56, 5747. Van Draanen, N. A.; Arseniyadis, S.; Crimmins, M. T.; Heathcock, C. H. J. Org. Chem. 1991, 56, 2499. Braun, M.; Sacha, H.; Angew. Chem., Int. Ed. Engl. 1991, 30, 1318. Gennari, C.; Hewkin, C. T.; Molinari, F.; Bernardi, A.; Comotti, A.; Goodman, J. M.; Paterson, I. J. Org. Chem. 1992, 57, 5173. Gennari, C.; Moresca, D.; Vieth, S.; Vulpetti, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1618. Oppolzer, W.; Lienard, P. Tetrahedron Lett. 1993, 34, 4321. Paterson, I.; Wallace, D. J.; Velazquez, S. M. Tetrahedron Lett. 1994, 35, 9083. Wang, Y.-C.; Hung, A.-W.; Chang, C. -S.; Van, T.-H.; J. Org. Chem. 1996, 61, 2038. Ghosh, A. K.; Ohnishi, M. J. Am. Chem. Soc. 1996, 118, 2527. Ghosh, A. K.; Fidanze, S.; Onishi, M.; Hussain, K. A. Tetrahedron Lett. 1997, 38, 7171. Li, Z.; Wu, R.; Michalczyk, R.; Dunlap, R. B.; Odom, J. D.; Silks, L. A. III J. Am. Chem. Soc. 2000, 122, 386.
43. Crotylboron tartrates were also considered: Roush, W. R.; Ando, K.; Powers, D. B.; Palkowitz, A. D.; Halterman, R. L. J. Am. Chem. Soc. 1990, 112, 6339 and references therein. Aldol routes include: Fleming, I. In Comprehensive Organic Synthesis, Vol. 2; Heathcock, C. H., Ed.; Pergamon Press: Oxford, 1991; p 563. Also see: Myers, A. G.; Widdowson, K. L J. Am. Chem. Soc. 1990, 112, 9672. Walker, M. A.; Heathcock, C. H. J. Org. Chem. 1991, 56, 5747. Van Draanen, N. A.; Arseniyadis, S.; Crimmins, M. T.; Heathcock, C. H. J. Org. Chem. 1991, 56, 2499. Braun, M.; Sacha, H.; Angew. Chem., Int. Ed. Engl. 1991, 30, 1318. Gennari, C.; Hewkin, C. T.; Molinari, F.; Bernardi, A.; Comotti, A.; Goodman, J. M.; Paterson, I. J. Org. Chem. 1992, 57, 5173. Gennari, C.; Moresca, D.; Vieth, S.; Vulpetti, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1618. Oppolzer, W.; Lienard, P. Tetrahedron Lett. 1993, 34, 4321. Paterson, I.; Wallace, D. J.; Velazquez, S. M. Tetrahedron Lett. 1994, 35, 9083. Wang, Y.-C.; Hung, A.-W.; Chang, C. -S.; Van, T.-H.; J. Org. Chem. 1996, 61, 2038. Ghosh, A. K.; Ohnishi, M. J. Am. Chem. Soc. 1996, 118, 2527. Ghosh, A. K.; Fidanze, S.; Onishi, M.; Hussain, K. A. Tetrahedron Lett. 1997, 38, 7171. Li, Z.; Wu, R.; Michalczyk, R.; Dunlap, R. B.; Odom, J. D.; Silks, L. A. III J. Am. Chem. Soc. 2000, 122, 386.
44. Crotylboron tartrates were also considered: Roush, W. R.; Ando, K.; Powers, D. B.; Palkowitz, A. D.; Halterman, R. L. J. Am. Chem. Soc. 1990, 112, 6339 and references therein. Aldol routes include: Fleming, I. In Comprehensive Organic Synthesis, Vol. 2; Heathcock, C. H., Ed.; Pergamon Press: Oxford, 1991; p 563. Also see: Myers, A. G.; Widdowson, K. L J. Am. Chem. Soc. 1990, 112, 9672. Walker, M. A.; Heathcock, C. H. J. Org. Chem. 1991, 56, 5747. Van Draanen, N. A.; Arseniyadis, S.; Crimmins, M. T.; Heathcock, C. H. J. Org. Chem. 1991, 56, 2499. Braun, M.; Sacha, H.; Angew. Chem., Int. Ed. Engl. 1991, 30, 1318. Gennari, C.; Hewkin, C. T.; Molinari, F.; Bernardi, A.; Comotti, A.; Goodman, J. M.; Paterson, I. J. Org. Chem. 1992, 57, 5173. Gennari, C.; Moresca, D.; Vieth, S.; Vulpetti, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1618. Oppolzer, W.; Lienard, P. Tetrahedron Lett. 1993, 34, 4321. Paterson, I.; Wallace, D. J.; Velazquez, S. M. Tetrahedron Lett. 1994, 35, 9083. Wang, Y.-C.; Hung, A.-W.; Chang, C. -S.; Van, T.-H.; J. Org. Chem. 1996, 61, 2038. Ghosh, A. K.; Ohnishi, M. J. Am. Chem. Soc. 1996, 118, 2527. Ghosh, A. K.; Fidanze, S.; Onishi, M.; Hussain, K. A. Tetrahedron Lett. 1997, 38, 7171. Li, Z.; Wu, R.; Michalczyk, R.; Dunlap, R. B.; Odom, J. D.; Silks, L. A. III J. Am. Chem. Soc. 2000, 122, 386.
45. Crotylboron tartrates were also considered: Roush, W. R.; Ando, K.; Powers, D. B.; Palkowitz, A. D.; Halterman, R. L. J. Am. Chem. Soc. 1990, 112, 6339 and references therein. Aldol routes include: Fleming, I. In Comprehensive Organic Synthesis, Vol. 2; Heathcock, C. H., Ed.; Pergamon Press: Oxford, 1991; p 563. Also see: Myers, A. G.; Widdowson, K. L J. Am. Chem. Soc. 1990, 112, 9672. Walker, M. A.; Heathcock, C. H. J. Org. Chem. 1991, 56, 5747. Van Draanen, N. A.; Arseniyadis, S.; Crimmins, M. T.; Heathcock, C. H. J. Org. Chem. 1991, 56, 2499. Braun, M.; Sacha, H.; Angew. Chem., Int. Ed. Engl. 1991, 30, 1318. Gennari, C.; Hewkin, C. T.; Molinari, F.; Bernardi, A.; Comotti, A.; Goodman, J. M.; Paterson, I. J. Org. Chem. 1992, 57, 5173. Gennari, C.; Moresca, D.; Vieth, S.; Vulpetti, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1618. Oppolzer, W.; Lienard, P. Tetrahedron Lett. 1993, 34, 4321. Paterson, I.; Wallace, D. J.; Velazquez, S. M. Tetrahedron Lett. 1994, 35, 9083. Wang, Y.-C.; Hung, A.-W.; Chang, C. -S.; Van, T.-H.; J. Org. Chem. 1996, 61, 2038. Ghosh, A. K.; Ohnishi, M. J. Am. Chem. Soc. 1996, 118, 2527. Ghosh, A. K.; Fidanze, S.; Onishi, M.; Hussain, K. A. Tetrahedron Lett. 1997, 38, 7171. Li, Z.; Wu, R.; Michalczyk, R.; Dunlap, R. B.; Odom, J. D.; Silks, L. A. III J. Am. Chem. Soc. 2000, 122, 386.
46. Crotylboron tartrates were also considered: Roush, W. R.; Ando, K.; Powers, D. B.; Palkowitz, A. D.; Halterman, R. L. J. Am. Chem. Soc. 1990, 112, 6339 and references therein. Aldol routes include: Fleming, I. In Comprehensive Organic Synthesis, Vol. 2; Heathcock, C. H., Ed.; Pergamon Press: Oxford, 1991; p 563. Also see: Myers, A. G.; Widdowson, K. L J. Am. Chem. Soc. 1990, 112, 9672. Walker, M. A.; Heathcock, C. H. J. Org. Chem. 1991, 56, 5747. Van Draanen, N. A.; Arseniyadis, S.; Crimmins, M. T.; Heathcock, C. H. J. Org. Chem. 1991, 56, 2499. Braun, M.; Sacha, H.; Angew. Chem., Int. Ed. Engl. 1991, 30, 1318. Gennari, C.; Hewkin, C. T.; Molinari, F.; Bernardi, A.; Comotti, A.; Goodman, J. M.; Paterson, I. J. Org. Chem. 1992, 57, 5173. Gennari, C.; Moresca, D.; Vieth, S.; Vulpetti, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1618. Oppolzer, W.; Lienard, P. Tetrahedron Lett. 1993, 34, 4321. Paterson, I.; Wallace, D. J.; Velazquez, S. M. Tetrahedron Lett. 1994, 35, 9083. Wang, Y.-C.; Hung, A.-W.; Chang, C. -S.; Van, T.-H.; J. Org. Chem. 1996, 61, 2038. Ghosh, A. K.; Ohnishi, M. J. Am. Chem. Soc. 1996, 118, 2527. Ghosh, A. K.; Fidanze, S.; Onishi, M.; Hussain, K. A. Tetrahedron Lett. 1997, 38, 7171. Li, Z.; Wu, R.; Michalczyk, R.; Dunlap, R. B.; Odom, J. D.; Silks, L. A. III J. Am. Chem. Soc. 2000, 122, 386.
47. Crotylboron tartrates were also considered: Roush, W. R.; Ando, K.; Powers, D. B.; Palkowitz, A. D.; Halterman, R. L. J. Am. Chem. Soc. 1990, 112, 6339 and references therein. Aldol routes include: Fleming, I. In Comprehensive Organic Synthesis, Vol. 2; Heathcock, C. H., Ed.; Pergamon Press: Oxford, 1991; p 563. Also see: Myers, A. G.; Widdowson, K. L J. Am. Chem. Soc. 1990, 112, 9672. Walker, M. A.; Heathcock, C. H. J. Org. Chem. 1991, 56, 5747. Van Draanen, N. A.; Arseniyadis, S.; Crimmins, M. T.; Heathcock, C. H. J. Org. Chem. 1991, 56, 2499. Braun, M.; Sacha, H.; Angew. Chem., Int. Ed. Engl. 1991, 30, 1318. Gennari, C.; Hewkin, C. T.; Molinari, F.; Bernardi, A.; Comotti, A.; Goodman, J. M.; Paterson, I. J. Org. Chem. 1992, 57, 5173. Gennari, C.; Moresca, D.; Vieth, S.; Vulpetti, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1618. Oppolzer, W.; Lienard, P. Tetrahedron Lett. 1993, 34, 4321. Paterson, I.; Wallace, D. J.; Velazquez, S. M. Tetrahedron Lett. 1994, 35, 9083. Wang, Y.-C.; Hung, A.-W.; Chang, C. -S.; Van, T.-H.; J. Org. Chem. 1996, 61, 2038. Ghosh, A. K.; Ohnishi, M. J. Am. Chem. Soc. 1996, 118, 2527. Ghosh, A. K.; Fidanze, S.; Onishi, M.; Hussain, K. A. Tetrahedron Lett. 1997, 38, 7171. Li, Z.; Wu, R.; Michalczyk, R.; Dunlap, R. B.; Odom, J. D.; Silks, L. A. III J. Am. Chem. Soc. 2000, 122, 386.
48. Crotylboron tartrates were also considered: Roush, W. R.; Ando, K.; Powers, D. B.; Palkowitz, A. D.; Halterman, R. L. J. Am. Chem. Soc. 1990, 112, 6339 and references therein. Aldol routes include: Fleming, I. In Comprehensive Organic Synthesis, Vol. 2; Heathcock, C. H., Ed.; Pergamon Press: Oxford, 1991; p 563. Also see: Myers, A. G.; Widdowson, K. L J. Am. Chem. Soc. 1990, 112, 9672. Walker, M. A.; Heathcock, C. H. J. Org. Chem. 1991, 56, 5747. Van Draanen, N. A.; Arseniyadis, S.; Crimmins, M. T.; Heathcock, C. H. J. Org. Chem. 1991, 56, 2499. Braun, M.; Sacha, H.; Angew. Chem., Int. Ed. Engl. 1991, 30, 1318. Gennari, C.; Hewkin, C. T.; Molinari, F.; Bernardi, A.; Comotti, A.; Goodman, J. M.; Paterson, I. J. Org. Chem. 1992, 57, 5173. Gennari, C.; Moresca, D.; Vieth, S.; Vulpetti, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1618. Oppolzer, W.; Lienard, P. Tetrahedron Lett. 1993, 34, 4321. Paterson, I.; Wallace, D. J.; Velazquez, S. M. Tetrahedron Lett. 1994, 35, 9083. Wang, Y.-C.; Hung, A.-W.; Chang, C. -S.; Van, T.-H.; J. Org. Chem. 1996, 61, 2038. Ghosh, A. K.; Ohnishi, M. J. Am. Chem. Soc. 1996, 118, 2527. Ghosh, A. K.; Fidanze, S.; Onishi, M.; Hussain, K. A. Tetrahedron Lett. 1997, 38, 7171. Li, Z.; Wu, R.; Michalczyk, R.; Dunlap, R. B.; Odom, J. D.; Silks, L. A. III J. Am. Chem. Soc. 2000, 122, 386.
49. Crotylboron tartrates were also considered: Roush, W. R.; Ando, K.; Powers, D. B.; Palkowitz, A. D.; Halterman, R. L. J. Am. Chem. Soc. 1990, 112, 6339 and references therein. Aldol routes include: Fleming, I. In Comprehensive Organic Synthesis, Vol. 2; Heathcock, C. H., Ed.; Pergamon Press: Oxford, 1991; p 563. Also see: Myers, A. G.; Widdowson, K. L J. Am. Chem. Soc. 1990, 112, 9672. Walker, M. A.; Heathcock, C. H. J. Org. Chem. 1991, 56, 5747. Van Draanen, N. A.; Arseniyadis, S.; Crimmins, M. T.; Heathcock, C. H. J. Org. Chem. 1991, 56, 2499. Braun, M.; Sacha, H.; Angew. Chem., Int. Ed. Engl. 1991, 30, 1318. Gennari, C.; Hewkin, C. T.; Molinari, F.; Bernardi, A.; Comotti, A.; Goodman, J. M.; Paterson, I. J. Org. Chem. 1992, 57, 5173. Gennari, C.; Moresca, D.; Vieth, S.; Vulpetti, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1618. Oppolzer, W.; Lienard, P. Tetrahedron Lett. 1993, 34, 4321. Paterson, I.; Wallace, D. J.; Velazquez, S. M. Tetrahedron Lett. 1994, 35, 9083. Wang, Y.-C.; Hung, A.-W.; Chang, C. -S.; Van, T.-H.; J. Org. Chem. 1996, 61, 2038. Ghosh, A. K.; Ohnishi, M. J. Am. Chem. Soc. 1996, 118, 2527. Ghosh, A. K.; Fidanze, S.; Onishi, M.; Hussain, K. A. Tetrahedron Lett. 1997, 38, 7171. Li, Z.; Wu, R.; Michalczyk, R.; Dunlap, R. B.; Odom, J. D.; Silks, L. A. III J. Am. Chem. Soc. 2000, 122, 386.
50. Crotylboron tartrates were also considered: Roush, W. R.; Ando, K.; Powers, D. B.; Palkowitz, A. D.; Halterman, R. L. J. Am. Chem. Soc. 1990, 112, 6339 and references therein. Aldol routes include: Fleming, I. In Comprehensive Organic Synthesis, Vol. 2; Heathcock, C. H., Ed.; Pergamon Press: Oxford, 1991; p 563. Also see: Myers, A. G.; Widdowson, K. L J. Am. Chem. Soc. 1990, 112, 9672. Walker, M. A.; Heathcock, C. H. J. Org. Chem. 1991, 56, 5747. Van Draanen, N. A.; Arseniyadis, S.; Crimmins, M. T.; Heathcock, C. H. J. Org. Chem. 1991, 56, 2499. Braun, M.; Sacha, H.; Angew. Chem., Int. Ed. Engl. 1991, 30, 1318. Gennari, C.; Hewkin, C. T.; Molinari, F.; Bernardi, A.; Comotti, A.; Goodman, J. M.; Paterson, I. J. Org. Chem. 1992, 57, 5173. Gennari, C.; Moresca, D.; Vieth, S.; Vulpetti, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1618. Oppolzer, W.; Lienard, P. Tetrahedron Lett. 1993, 34, 4321. Paterson, I.; Wallace, D. J.; Velazquez, S. M. Tetrahedron Lett. 1994, 35, 9083. Wang, Y.-C.; Hung, A.-W.; Chang, C. -S.; Van, T.-H.; J. Org. Chem. 1996, 61, 2038. Ghosh, A. K.; Ohnishi, M. J. Am. Chem. Soc. 1996, 118, 2527. Ghosh, A. K.; Fidanze, S.; Onishi, M.; Hussain, K. A. Tetrahedron Lett. 1997, 38, 7171. Li, Z.; Wu, R.; Michalczyk, R.; Dunlap, R. B.; Odom, J. D.; Silks, L. A. III J. Am. Chem. Soc. 2000, 122, 386.
51. Crotylboron tartrates were also considered: Roush, W. R.; Ando, K.; Powers, D. B.; Palkowitz, A. D.; Halterman, R. L. J. Am. Chem. Soc. 1990, 112, 6339 and references therein. Aldol routes include: Fleming, I. In Comprehensive Organic Synthesis, Vol. 2; Heathcock, C. H., Ed.; Pergamon Press: Oxford, 1991; p 563. Also see: Myers, A. G.; Widdowson, K. L J. Am. Chem. Soc. 1990, 112, 9672. Walker, M. A.; Heathcock, C. H. J. Org. Chem. 1991, 56, 5747. Van Draanen, N. A.; Arseniyadis, S.; Crimmins, M. T.; Heathcock, C. H. J. Org. Chem. 1991, 56, 2499. Braun, M.; Sacha, H.; Angew. Chem., Int. Ed. Engl. 1991, 30, 1318. Gennari, C.; Hewkin, C. T.; Molinari, F.; Bernardi, A.; Comotti, A.; Goodman, J. M.; Paterson, I. J. Org. Chem. 1992, 57, 5173. Gennari, C.; Moresca, D.; Vieth, S.; Vulpetti, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1618. Oppolzer, W.; Lienard, P. Tetrahedron Lett. 1993, 34, 4321. Paterson, I.; Wallace, D. J.; Velazquez, S. M. Tetrahedron Lett. 1994, 35, 9083. Wang, Y.-C.; Hung, A.-W.; Chang, C. -S.; Van, T.-H.; J. Org. Chem. 1996, 61, 2038. Ghosh, A. K.; Ohnishi, M. J. Am. Chem. Soc. 1996, 118, 2527. Ghosh, A. K.; Fidanze, S.; Onishi, M.; Hussain, K. A. Tetrahedron Lett. 1997, 38, 7171. Li, Z.; Wu, R.; Michalczyk, R.; Dunlap, R. B.; Odom, J. D.; Silks, L. A. III J. Am. Chem. Soc. 2000, 122, 386.
52. (a) Danda, H.; Hansen, M. M.; Heathcock, C. H. J. Org. Chem. 1990, 55, 172
53. (b) Walker, M. A.; Heathcock, C. H. J. Org. Chem. 1991, 56, 4747.
54. Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127.
55. (a) Abiko, A.; Liu, J.-F.; Masamune, S. J. Am. Chem. Soc. 1997, 119, 2586
56. (b) Yoshimitsu, T.; Song, J. J.; Wang, G. Q.; Masamune, S. J. Org. Chem. 1997, 62, 8968
57. 1H NMR and HPLC analysis. No syn-aldol products were observed. The diastereomerics were readily separated by flash chromatography.
58. Coste, J.; Ferot, E.; Jouin, P.; Castro, B. Tetrahedron Lett. 1991, 32, 1967. The amine for 6i was obtained by EDCI coupling of ethanolamine to stearic acid (86%).
59. See ref 7b and: Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467.
60. See the Supporting Information.
61. ent-4ej was produced in analogous fashion using the enantiomeric form of the norephedrine ester. See supplementary data.
62. Wilson, W. H.; Jamis-Dow, C.; Bryant G. J. Clin. Oncol. 1995, 13, 1985
63. (b) Kayes, S. B. Br. Cancer 1993, 67, 641.