Concise, biomimetic total synthesis of d,l-marcfortine C

Tetrahedron

Volumn 63, Issue 27, 2007, Pages 6124-6130

  Greshock, Thomas J ^a   Grubbs, Alan W ^a   Williams, Robert M ^a,b  

^a Department of Environmental and Radiological Health Sciences   (United States)

^b UNIVERSITY OF COLORADO CANCER CENTER   (United States)

Author keywords

Azadiene; Diels Alder; Indole; Marcfortine; Natural product

Indexed keywords

FUNGAL PROTEIN; INDOLE; INDOLE ALKALOID; MARCFORTINE A; MARCFORTINE B; MARCFORTINE C; NORGEAMIDE A; NORGEAMIDE B; NOTOAMIDE A; NOTOAMIDE B; NOTOAMIDE C; NOTOAMIDE D; OXAZIRIDINE DERIVATIVE; STEPHACIDIN A; UNCLASSIFIED DRUG;

ARTICLE; BIOMIMETICS; CONTROLLED STUDY; DIELS ALDER REACTION; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; MOLECULAR INTERACTION; NONHUMAN; OXIDATION; PINACOL REARRANGEMENT; PRIORITY JOURNAL; STEREOCHEMISTRY;

ALNUS;

EID: 34249075399     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.03.016     Document Type: Article

References (52)

1. Yamazaki M., and Okuyama E. Tetrahedron Lett. 22 (1981) 135
2. Ondeyka J.G., Goegelman R.T., Schaeffer J.M., Kelemen L., and Zitano L. J. Antibiot. 43 (1990) 1375
3. Liesch J.M., and Wichmann C.F. J. Antibiot. 43 (1990) 1380
4. Banks R.M., Blanchflower S.E., Everett J.R., Manfer B.R., and Reading C.J. J. Antibiot. 50 (1997) 840
5. Birch A.J., and Wright J.J. J. Chem. Soc., Chem. Commun. (1969) 644
6. Birch A.J., and Wright J.J. Tetrahedron 26 (1970) 2329
7. Birch A.J., and Russell R.A. Tetrahedron 28 (1972) 2999
8. Bird B.A., Remaley A.T., and Campbell I.M. Appl. Environ. Microbiol. 42 (1981) 521
9. Bird B.A., and Campbell I.M. Appl. Environ. Microbiol. 43 (1982) 345
10. Robbers J.E., and Straus J.W. Lloydia 38 (1975) 355
11. Paterson R.R.M., and Hawksworth D.L. Trans. Br. Mycol. Soc. 85 (1985) 95
12. Wilson B.J., Yang D.T.C., and Harris T.M. Appl. Microbiol. 26 (1973) 633
13. Coetzer J. Acta Crystallogr. B30 (1974) 2254
14. Qian-Cutrone J., Huang S., Shu Y.-Z., Vyas D., Fairchild C., Menendez A., Krampitz K., Dalterio R., Klohr S.E., and Gao Q. J. Am. Chem. Soc. 124 (2002) 14556
15. Qian-Cutrone, J.; Krampitz, K.; Shu, Y.-Z.; Chang, L. P. U.S. Patent 6,291,461, 2001.
16. Kato H., Yoshida T., Tokue T., Nojiri Y., Hirota H., Ohta T., Williams R.M., and Tsukamoto S. Angew. Chem., Int. Ed. 46 (2007) 2254
17. Williams R.M., and Cox R.J. Acc. Chem. Res. 36 (2003) 127
18. Williams R.M. Chem. Pharm. Bull. 50 (2002) 711
19. Williams R.M., Stocking E.M., and Sanz-Cevera J.F. Top. Curr. Chem. 209 (2000) 98
20. Polonsky J., Merrien M.-A., Prangé T., and Pascard C. J. Chem. Soc., Chem. Commun. (1980) 601
21. Prangé T., Billion M.-A., Vuilhorgne M., Pascard C., and Polonsky J. Tetrahedron Lett. 22 (1981) 1977
22. For anthelminthic activity of the marcfortines and derivatives, see: Mrozik, H. U.S. Patent 4,866,060, 1989;
23. Blizzard, T. A.; Mrozik, H. U.S. Patent 4,923,867, 1990;
24. For the synthesis of marcfortine A derivatives, see:
25. Lee B.H., and Clothier M.F. J. Org. Chem. 62 (1997) 1863
26. Lee B.H., and Clothier M.F. Bioorg. Med. Chem. Lett. 8 (1998) 3415 and references cited therein
27. Herzon S.B., and Myers A.G. J. Am. Chem. Soc. 127 (2005) 5342
28. Myers A.G., and Herzon S.B. J. Am. Chem. Soc. 125 (2003) 12080
29. Baran P.S., Guerrero C.A., Ambhaikar N.B., and Hafensteiner B.D. Angew. Chem., Int. Ed. 44 (2005) 606
30. Baran P.S., Guerrero C.A., Hafensteiner B.D., and Ambhaikar N.B. Angew. Chem., Int. Ed. 44 (2005) 3892
31. Baran P.S., Hafensteiner B.D., Ambhaikar N.B., Guerrero C.A., and Gallagher J.D. J. Am. Chem. Soc. 128 (2006) 8678
32. Grubbs A.W., Artman III G.D., Tsukamoto S., and Williams R.M. Angew. Chem., Int. Ed. 46 (2007) 2257
33. Greshock T.J., Grubbs A.W., Tsukamoto S., and Williams R.M. Angew. Chem., Int. Ed. 46 (2007) 2262
34. Baldas J., Birch A.J., and Russell R.A. J. Chem. Soc., Perkin Trans. 1 (1974) 50
35. Porter A.E.A., and Sammes P.G. J. Chem. Soc., Chem. Commun. (1970) 1103
36. Williams R.M., Sanz-Cervera J.F., Sancenón F., Marco J.A., and Halligan K. J. Am. Chem. Soc. 120 (1998) 1090
37. Stocking E.M., Sanz-Cervera J.F., and Williams R.M. J. Am. Chem. Soc. 122 (2000) 1675
38. Adams L.A., Valente M.W.N., and Williams R.M. Tetrahedron 62 (2006) 5195
39. Grubbs A.W., Artman III G.D., and Williams R.M. Tetrahedron Lett. 46 (2005) 9013
40. 2, ethanol, reflux
41. Davis F.A., Townson J.C., Vashi D.B., Thimma Ready R., McCauley J.P., Harakal M.E., and Gosciniak D.J. J. Org. Chem. 55 (1990) 1254
42. Snider B.B., and Zeng H. J. Org. Chem. 68 (2003) 545
43. Our group has previously achieved oxidation of the C2-C3 double bond using mCPBA and t-BuOCl, see:
44. Williams R.M., Glinka T., Kwast E., and Coffman H. J. Am. Chem. Soc. 112 (1990) 808
45. Cushing T.D., Sanz-Cevera J.F., and Williams R.M. J. Am. Chem. Soc. 118 (1996) 557
46. Williams R.M., Glinka T., and Kwast E. Tetrahedron Lett. 30 (1989) 5575
47. For previous one-pot procedures generating oxindoles from indole, see:
48. Finch N., and Taylor W.I. J. Am. Chem. Soc. 84 (1962) 1318
49. Hollinshead S.P., Grubisha D.S., Bennett D.W., and Cook J.M. Heterocycles 29 (1989) 529
50. Edmondson S., Danishefsky S.J., Sepp-Lorenzino L., and Rosen N. J. Am. Chem. Soc. 121 (1999) 2147
51. Wang H., and Ganesan A. J. Org. Chem. 65 (2000) 4685
52. A total synthesis of the related alkaloid, d,l-marcfortine B (2) was very recently published, see:. Trost B.M., Cramer N., and Bernsmann H. J. Am. Chem. Soc. 129 (2007) (published on-line February 22, 2007)