Synthetic studies directed toward the phorboxazoles: Preparation of the C3-C15 bisoxane segment and two stereoisomers

Tetrahedron

Volumn 58, Issue 30, 2002, Pages 6009-6018

  Greer, Patrick B ^a   Donaldson, William A ^a  

^a Marquette University   (United States)

Author keywords

C3 C15 bisoxane segment; Phorboxazoles; Stereoisomers

Indexed keywords

4 NITROBENZOIC ACID; ALCOHOL DERIVATIVE; ALDEHYDE; ALKADIENE; ALKANE DERIVATIVE; CARBENE; CHLORIDE; ESTER DERIVATIVE; GLUCOSIDE; LEWIS ACID; MARINE TOXIN; PYRAN; PYRONE DERIVATIVE; VINYL DERIVATIVE;

ALLYLATION; ARTICLE; CATALYSIS; DRUG CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; ESTERIFICATION; HYDROLYSIS; MITSUNOBU REACTION; OZONOLYSIS; POLYMERIZATION; PRIORITY JOURNAL; RING CLOSING METATHESIS; STEREOISOMERISM;

EID: 0037157810     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)00613-0     Document Type: Article

References (58)

1. (a) Searle P.A., Molinski T.F. J. Am. Chem. Soc. 117:1995;8126-8131
2. (b) Searle P.A., Molinski T.F., Brzezinski L.J., Leahy J.W. J. Am. Chem. Soc. 118:1996;9422-9423
3. (c) Molinski T.F. Tetrahedron Lett. 37:1996;7879-7880.
4. (a) Lee C.S., Forsyth C.J. Tetrahedron Lett. 37:1996;6649-6652
5. (b) Cink R.D., Forsyth C.J. J. Org. Chem. 62:1997;5672-5673
6. (c) Ahmed F., Forsyth C.J. Tetrahedron Lett. 39:1998;183-186
7. (d) Evans D.A., Cee V.J., Smith T.E., Santiago K.J. Org. Lett. 1:1999;87-90
8. (e) Smith A.B. III, Verhoest P.R., Minbiole K.P. Org. Lett. 1:1999;909-912
9. (f) Smith A.B. III, Minbiole K.P., Verhoest P.R., Beauchamp T.J. Org. Lett. 1:1999;913-916
10. (g) Williams D.R., Clark M.P., Berliner M.A. Tetrahedron Lett. 40:1999;2287-2290
11. (h) Williams D.R., Clark M.P. Tetrahedron Lett. 40:1999;2291-2294
12. (h) Williams D.R., Clark M.P. Org. Lett. 2:2000;3023-3026
13. (j) Ye T., Pattenden G. Tetrahedron Lett. 39:1998;319-322
14. (k) Pattenden G., Plowright A.T., Tornos J.A., Ye T. Tetrahedron Lett. 39:1998;6099-6102
15. (l) Pattenden G., Plowright A.T. Tetrahedron Lett. 41:2000;983-986
16. (m) Wolbers P., Hoffmann H.M.R. Tetrahedron. 55:1999;1905-1914
17. (n) Wolbers P., Hoffmann H.M.R. Synthesis. 1999;797-802
18. (o) Misske A.M., Hoffmann H.M.R. Tetrahedron. 55:1999;4315-4324
19. (p) Wolbers P., Misske A.M., Hoffmann H.M.R. Tetrahedron Lett. 40:1999;4527-4530
20. (q) Wolbers P., Hoffmann H.M.R., Sasse F. Synlett. 1999;1808-1810
21. (r) Paterson I., Arnott E.A. Tetrahedron Lett. 39:1998;7185-7188
22. (s) Rychnovsky S.D., Thomas C.R. Org. Lett. 2:2000;1217-1219
23. (t) Schaus J.V., Panek J.S. Org. Lett. 2:2000;469-471
24. (u) White J.D., Kranemann C.L., Kuntiyong P. Org. Lett. 3:2001;4003-4006.
25. (a) Forsyth C.J., Ahmed F., Cink R.D., Lee C.S. J. Am. Chem. Soc. 120:1998;5597-5598
26. (b) Evans D.A., Cee V.J., Smith T.E., Fitch D.M., Cho P.S. Angew. Chem., Int. Ed. Engl. 39:2000;2533-2536
27. (c) Evans D.A., Fitch D.M. Angew. Chem., Int. Ed. Engl. 39:2000;2536-2540
28. (d) Evans D.A., Fitch D.M., Smith T.E., Cee V.J. J. Am. Chem. Soc. 122:2000;10033-10046
29. (e) Smith A.B. III, Verhoest P.R., Minbiole K.P., Schelhaas M. J. Am. Chem. Soc. 123:2001;4834-4836
30. (f) Smith A.B. III, Minbiole K.P., Verhoest P.R., Schelhaas M. J. Am. Chem. Soc. 123:2001;10942-10953.
31. Preliminary communication: Greer P.B., Donaldson W.A. Tetrahedron Lett. 41:2000;3801-3803.
32. (a) Danishefsky S., Bilodeau M.T. Angew. Chem., Int. Ed. Engl. 35:1996;1380-1419
33. (b) Danishefsky S., Bilodeau M.T. Aldrichimica Acta 19:1986;59-69
34. (a) Bednarski M., Danishefsky S. J. Am. Chem. Soc. 108:1986;7060-7067
35. (b) Danishefsky S., Bednarski M., Izawa T., Maring C. J. Org. Chem. 49:1984;2290-2292.
36. Keck G.E., Li X.-Y., Krishnamurthy D. J. Org. Chem. 60:1995;5998-5999.
37. Danishefsky S., Langer M. J. Org. Chem. 50:1985;3672-3674.
38. (a) Lewis M.D., Cha J.K., Kishi Y. J. Am. Chem. Soc. 104:1982;4976-4978
39. (b) Paterson I., Cumming J.G. Tetrahedron Lett. 33:1992;2847-2850
40. (c) Romero J.A.C., Tabacco S.A., Woerpel K.A. J. Am. Chem. Soc. Lett. 122:2000;168-169
41. Hosomi A., Sakata Y., Sakurai H. Tetrahedron Lett. 25:1984;2383-2386.
42. (a) Wincott F.E., Danishefsky S.J., Schulte G. Tetrahedron Lett. 28:1987;4951-4954
43. (b) Danishefsky S.J., Armistead D.M., Wincott F.E., Selnick H.G., Hungate R. J. Am. Chem. Soc. 111:1989;2967-2980.
44. For other recent applications of this strategy see: (a) Cossy J., Bauer D., Bellosta V. Tetrahedron Lett. 40:1999;4187-4188 (b) Ghosh A.K., Liu C. Chem. Commun. 1999;1743-1744 (c) Ramachandran P.V., Reddy M.V.R., Brown H.C. Tetrahedron Lett. 41:2000;583-586 (d) Hunter T.J., O'Doherty G.A. Org. Lett. 3:2001;2777-2780 (e) Du Y., Weimer D.F. Tetrahedron Lett. 42:2001;6069-6072.
45. For other recent applications of this strategy see: (a) Cossy J., Bauer D., Bellosta V. Tetrahedron Lett. 40:1999;4187-4188 (b) Ghosh A.K., Liu C. Chem. Commun. 1999;1743-1744 (c) Ramachandran P.V., Reddy M.V.R., Brown H.C. Tetrahedron Lett. 41:2000;583-586 (d) Hunter T.J., O'Doherty G.A. Org. Lett. 3:2001;2777-2780 (e) Du Y., Weimer D.F. Tetrahedron Lett. 42:2001;6069-6072.
46. For other recent applications of this strategy see: (a) Cossy J., Bauer D., Bellosta V. Tetrahedron Lett. 40:1999;4187-4188 (b) Ghosh A.K., Liu C. Chem. Commun. 1999;1743-1744 (c) Ramachandran P.V., Reddy M.V.R., Brown H.C. Tetrahedron Lett. 41:2000;583-586 (d) Hunter T.J., O'Doherty G.A. Org. Lett. 3:2001;2777-2780 (e) Du Y., Weimer D.F. Tetrahedron Lett. 42:2001;6069-6072.
47. For other recent applications of this strategy see: (a) Cossy J., Bauer D., Bellosta V. Tetrahedron Lett. 40:1999;4187-4188 (b) Ghosh A.K., Liu C. Chem. Commun. 1999;1743-1744 (c) Ramachandran P.V., Reddy M.V.R., Brown H.C. Tetrahedron Lett. 41:2000;583-586 (d) Hunter T.J., O'Doherty G.A. Org. Lett. 3:2001;2777-2780 (e) Du Y., Weimer D.F. Tetrahedron Lett. 42:2001;6069-6072.
48. For other recent applications of this strategy see: (a) Cossy J., Bauer D., Bellosta V. Tetrahedron Lett. 40:1999;4187-4188 (b) Ghosh A.K., Liu C. Chem. Commun. 1999;1743-1744 (c) Ramachandran P.V., Reddy M.V.R., Brown H.C. Tetrahedron Lett. 41:2000;583-586 (d) Hunter T.J., O'Doherty G.A. Org. Lett. 3:2001;2777-2780 (e) Du Y., Weimer D.F. Tetrahedron Lett. 42:2001;6069-6072.
49. (a) Brown H.C., Jadhav P.K. J. Am. Chem. Soc. 105:1983;2092-2093
50. (b) Racherla U.S., Brown H.C. J. Org. Chem. 56:1991;401-404.
51. Dale J.A., Mosher H.S. J. Am. Chem. Soc. 95:1973;512-519.
52. 12d The product can be formed in greater yield via coupling of the alcohol with acrylic acid in the presence of DCC.
53. Grubbs R.H. Tetrahedron. 54:1998;4413-4450.
54. Due to an error in weighing, nearly 1 equiv. of Grubbs' catalyst was used in the preparation of (+)-7. It is anticipated that the reaction would proceed with catalytic amounts of this reagent, based on the preparations of (-)-5 and (+)-6.
55. (a) Nerenberg J.B., Hung D.T., Somers P.K., Schreiber S.L. J. Am. Chem. Soc. 115:1993;12621-12622
56. (b) Boger D.L., Hong J. J. Am. Chem. Soc. 123:2001;8515-8519.
57. Mitsunobu O. Synthesis. 1981;1-28.
58. Ndibwami A., Lamothe S., Guay D., Plante R., Soucy P., Goldstein S., Deslongchamps P. Can. J. Chem. 71:1993;695-712.