Total synthesis of erythromycin B

Tetrahedron

Volumn 63, Issue 26, 2007, Pages 5709-5729

  Breton, Philippe ^a   Hergenrother, Paul J ^a   Hida, Tsuneaki ^a   Hodgson, Anne ^a   Judd, Andrew S ^a   Kraynack, Erica ^a   Kym, Philip R ^a   Lee, Wen Cherng ^a   Loft, Michael S ^a   Yamashita, Masayuki ^a   Martin, Stephen F ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BERYTHROMYCIN; DIOXABICYCLO[3.3.1]NONENONE; FURAN; KETONE DERIVATIVE; LACTONE; MACROCYCLIC COMPOUND; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CYCLIZATION; DRUG SYNTHESIS; GLYCOSYLATION; METHODOLOGY; OXIDATION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 34249058524     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.02.044     Document Type: Article

References (67)

1. McGuire J.M., Bunch R.L., Anderson R.C., Boaz H.E., Flynn E.H., Powell H.M., and Smith J.W. Antibiot. Chemother. 2 (1952) 281
2. In: Omura S. (Ed). Macrolide Antibiotics (1984), Academic, Orlando, FL
3. Pal S. Tetrahedron 62 (2006) 3171
4. Vester B., and Douthwaite S. Antimicrob. Agents Chemother. 45 (2001) 1
5. Schlünzen F., Zarivach R., Harms J., Bashan A., Tocilj A., Albrecht R., Yonath A., and Franceschi F. Nature 413 (2001) 814
6. Hansen J.L., Ippolito J.A., Ban N., Nissen P., Moore P.B., and Steitz T.A. Mol. Cells 10 (2002) 117
7. For leading references and representative synthetic approaches, see:
8. Corey E.J., Hopkins P.B., Kim S., Yoo S., Nambiar K.P., and Falck J.R. J. Am. Chem. Soc. 101 (1979) 7131
9. Masamune S., Hirama M., Mori S., Ali S.A., and Garvey D.S. J. Am. Chem. Soc. 103 (1981) 1568
10. Bernet B., Bishop P.M., Caron M., Kawamata T., Roy B.L., Ruest L., Sauvé G., Soucy P., and Deslongchamps P. Can. J. Chem. 63 (1985) 2810 2814, 2818
11. Stork G., and Rychnovsky S.D. J. Am. Chem. Soc. 109 (1987) 1565
12. Chamberlin A.R., Dezube M., Reich S.H., and Sall D.J. J. Am. Chem. Soc. 111 (1989) 6247
13. Paterson I., and Rawson D.J. Tetrahedron Lett. 30 (1989) 7463
14. Nakata M., Arai M., Tomooka K., Ohsawa N., and Kinoshita M. Bull. Chem. Soc. Jpn. 62 (1989) 2618
15. Hikota M., Tone H., Horita K., and Yonemitsu O. J. Org. Chem. 55 (1990) 7
16. Myles D.C., Danishefsky S.J., and Schulte G. J. Org. Chem. 55 (1990) 1636
17. Hikota M., Tone H., Horita K., and Yonemitsu O. Tetrahedron 46 (1990) 4613
18. Sviridov A.F., Borodkin V.S., Ermolenko M.S., Yashunsky D.V., and Kochetkov N.K. Tetrahedron 47 (1991) 2291 2317
19. Mulzer J., Mareski P.A., Buschmann J., and Luger P. Synthesis (1992) 215
20. Stürmer R., Ritter K., and Hoffmann R.W. Angew. Chem., Int. Ed. Engl. 32 (1993) 105
21. Evans D.A., Kim A.S., Metternich R., and Novack V.J. J. Am. Chem. Soc. 120 (1998) 5921
22. Peng Z.-H., and Woerpel K.A. J. Am. Chem. Soc. 125 (2003) 6018
23. Muri D., Lohse-Fraefel N., and Carreira E.M. Angew. Chem., Int. Ed. 44 (2005) 4036
24. Crimmins M.T., and Slade D.J. Org. Lett. 8 (2006) 2191
25. Woodward R.B., Logusch E., Nambiar K.P., Sakan K., Ward D.E., Au-Yeung B.-W., Balaram P., Browne L.J., Card P.J., Chen C.H., Chênevert R.B., Fliri A., Frobel K., Gais H.-J., Garratt D.G., Hayakawa K., Heggie W., Hesson D.P., Hoppe D., Hoppe I., Hyatt J.A., Ikeda D., Jacobi P.A., Kim K.S., Kobuke Y., Kojima K., Krowicki K., Lee V.J., Leutert T., Malchenko S., Martens J., Matthews R.S., Ong B.S., Press J.B., Rajan Babu T.V., Rousseau G., Sauter H.M., Suzuki M., Tatsuta K., Tolbert L.M., Truesdale E.A., Uchida I., Ueda Y., Uyehara T., Vasella A.T., Vladuchick W.C., Wade P.A., Williams R.M., and Wong H.N.-C. J. Am. Chem. Soc. 103 (1981) 3210 3213, 3215
26. Nakata T., Fukui M., and Oishi T. Tetrahedron Lett. 29 (1988) 2219 2223
27. Cane D.E., Lambalot R.H., Prabhakaran P.C., and Ott W.R. J. Am. Chem. Soc. 115 (1993) 522
28. Andersen J.F., Tatsuta K., Gunji H., Ishiyama T., and Hutchinson C.R. Biochemistry 32 (1993) 1905
29. Martin S.F., Hida T., Kym P.R., Loft M., and Hodgson A. J. Am. Chem. Soc. 119 (1997) 3193
30. Hergenrother P.J., Hodgson A., Judd A.S., Lee W.C., and Martin S.F. Angew. Chem., Int. Ed. 42 (2003) 3278
31. Martin S.F., Gluchowski C., Campbell C.L., and Chapman R.C. Tetrahedron 44 (1988) 3171
32. For a preliminary report of these studies, see:. Martin S.F., and Yamashita M. J. Am. Chem. Soc. 113 (1991) 5478
33. 2, EtOH, rt (93%).
34. Flynn E.H., Sigal Jr. M.V., Wiley P.F., and Gerzon K. J. Am. Chem. Soc. 76 (1954) 3121
35. Flynn E.H., Murphy H.W., and McMahon R.E. J. Am. Chem. Soc. 77 (1955) 3104
36. Jones P.H., and Rowley E.K. J. Org. Chem. 33 (1968) 665
37. Freiberg, L. A. U.S. Patent 3,725,385, 1973;
38. Hunt E., Knowles D.J.C., Shillingford C., Wilson J.M., and Zomaya I.I. J. Antibiot. 42 (1989) 293
39. 2, rt (74%). (c) NaH, THF, 0 °C (81%).
40. Siedlecka R., Skarzewski J., and Mlochowski J. Tetrahedron Lett. 31 (1990) 2177
41. Bal B.S., Childers Jr. W.E., and Pinnick H.W. Tetrahedron 37 (1981) 2091
42. 2, 2-methyl-2-butene, aq t-BuOH, rt (78% for two steps).
43. Inanaga J., Hirata K., Saeki H., Katsuki T., and Yamaguchi M. Bull. Chem. Soc. Jpn. 52 (1979) 1989
44. Corey E.J., and Nicolaou K.C. J. Am. Chem. Soc. 96 (1974) 5614
45. 3, rt.
46. 2, 2-methyl-2-butene, aq t-BuOH, rt (73%); (h) TBAF, HMPA, 80 °C (76%).
47. 4NI, KH, 18-crown-6, THF (92%).
48. Boden E.P., and Keck G.E. J. Org. Chem. 50 (1985) 2394
49. Martin S.F., Pacofsky G.J., Gist R.P., and Lee-C W. J. Am. Chem. Soc. 111 (1989) 7634
50. Martin S.F., Lee W.-C., Pacofsky G.J., Gist R.P., and Mulhern T.A. J. Am. Chem. Soc. 116 (1994) 4674
51. Martin S.F., and Lee W.-C. Tetrahedron Lett. 34 (1993) 2711
52. For a leading reference to double stereodifferentiating aldol reactions, see:. Evans D.A., Dart M.J., Duffy J.L., and Rieger D.L. J. Am. Chem. Soc. 117 (1995) 9073
53. Evans D.A., Chapman K.T., and Carreira E.M. J. Am. Chem. Soc. 110 (1988) 3560
54. Oikawa Y., Nishi T., and Yonemitsu O. Tetrahedron Lett. 24 (1983) 4037
55. Horita K., and Yonemitsu O. Chem. Pharm. Bull. 37 (1989) 1719
56. Dess D.B., and Martin J.C. J. Org. Chem. 48 (1983) 4155
57. Dess D.B., and Martin J.C. J. Am. Chem. Soc. 113 (1991) 7277
58. Ireland R.E., and Liu L. J. Org. Chem. 58 (1993) 2899
59. Toshima K., Nozaki Y., Mukaiyama S., Tamai T., Nakata M., Tatsuta K., and Kinoshita M. J. Am. Chem. Soc. 117 (1995) 3717
60. The corresponding β-anomer was also isolated in 10% yield (17% based upon recovered starting material).
61. For example, see:. Kong X., and Grindley T.B. Can. J. Chem. 72 (1994) 2396 and references therein
62. Tolstikov G.A., Miftakhov M.S., Adler M.E., Komissarova N.G., Kuznetsov O.M., and Vostrikov N.S. Synthesis (1989) 940
63. Evans D.A., Nelson J.V., Vogel E., and Taber T.R. J. Am. Chem. Soc. 103 (1981) 3099
64. Crimmins M.T., King B.W., Tabet E.A., and Chaudhary K. J. Org. Chem. 66 (2001) 894
65. Crimmins M.T., and Chaudhary K. Org. Lett. 2 (2000) 775
66. Travis B.R., Narayan R.S., and Borhan B. J. Am. Chem. Soc. 124 (2002) 3824
67. Still W.C., Kahn M., and Mitra A. J. Org. Chem. 43 (1978) 2923