Total synthesis of haouamine A: the indeno-tetrahydropyridine core

Tetrahedron

Volumn 65, Issue 33, 2009, Pages 6600-6610

  Burns, Noah Z ^a   Jessing, Mikkel ^a   Baran, Phil S ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HAOUAMINE A; NATURAL PRODUCT; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CYCLIZATION; ENANTIOSELECTIVITY; PINACOL REARRANGEMENT; PRIORITY JOURNAL; REACTION ANALYSIS; STEVENS REARRANGEMENT; SYNTHESIS;

EID: 67650254237     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.05.075     Document Type: Article

References (40)

1. Garrido L., Zubía E., Ortega M.J., and Salvá J. J. Org. Chem. 68 (2003) 293-299
2. For a theoretical investigation of this dynamic equilibrium, see:. Belostotskii A.M. J. Org. Chem. 73 (2008) 5723-5731
3. Baran P.S., and Burns N.Z. J. Am. Chem. Soc. 128 (2006) 3908-3909
4. Burns N.Z., and Baran P.S. Angew. Chem., Int. Ed. 47 (2008) 205-208
5. Smith N.D., Hayashida J., and Rawal V.H. Org. Lett. 7 (2005) 4309-4312
6. Grundl M.A., and Trauner D. Org. Lett. 8 (2006) 23-25
7. Wipf P., and Furegati M. Org. Lett. 8 (2006) 1901-1904
8. Jeong J.H., and Weinreb S.M. Org. Lett. 8 (2006) 2309-2312
9. Fürstner A., and Ackerstaff J. Chem. Commun. (2008) 2870-2872
10. Taniguchi T., Zaimoku H., and Ishibashi H. J. Org. Chem. 74 (2009) 2624-2626
11. Retracted article:. Gravel E., Poupon E., and Hocquemiller R. Chem. Commun. (2007) 719-721
12. Chichibabin A.E. J. Russ. Phys. Chem. Soc. 37 (1906) 1229
13. Chichibabin A.E. J. Prakt. Chem. 107 (1924) 122-128
14. Eliel E.L., McBride R.T., and Kaufmann S. J. Am. Chem. Soc. 75 (1953) 4291-4296
15. Farley C.P., and Eliel E.L. J. Am. Chem. Soc. 78 (1956) 3477-3484
16. Eckroth D.R. Chem. Ind. (London) (1967) 920-921
17. Panzella L., Di Donato P., Comes S., Napolitano A., Palumbo A., and d'Ischia M. Tetrahedron Lett. 46 (2005) 6457-6460
18. For a review, see:. Markó I.E. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 3 (1991), Pergamon, Oxford 913-974
19. Hofmann A.W. Ann. 78 (1851) 253-281
20. Littke A.F., and Fu G.C. J. Am. Chem. Soc. 123 (2001) 6989-7000
21. Herrmann W.A., Brossmer C., Öfele K., Reisinger C.-P., Priermeier T., Beller M., and Fischer H. Angew. Chem., Int. Ed. Engl. 34 (1995) 1844-1848
22. Minuti L., Taticchi A., Marrocchi A., Lanari D., Broggi A., and Gacs-Baitz E. Tetrahedron: Asymmetry 14 (2003) 481-487
23. Davies H.M.L., and Manning J.R. Nature 451 (2008) 417-424
24. Dondas H.A., Grigg R., Hadjisoteriou M., Markandu J., Kennewell P., and Thornton-Pett M. Tetrahedron 57 (2001) 1119-1128
25. Cicchi S., Bonanni M., Cardona F., Revuelta J., and Goti A. Org. Lett. 5 (2003) 1773-1776
26. Trost B.M., and Schroeder G.M. J. Am. Chem. Soc. 121 (1999) 6759-6760
27. Trost B.M., Schroeder G.M., and Kristensen J. Angew. Chem., Int. Ed. 41 (2002) 3492-3495
28. Trost B.M., and Schroeder G.M. Chem.-Eur. J. 11 (2005) 174-184
29. For a review, see:. Enders D., and Klatt M. Synthesis (1996) 1403-1418
30. Dolling U.-H., Davis P., and Grabowski E.J.J. J. Am. Chem. Soc. 106 (1984) 446-447
31. Bhattacharya A., Dolling U.-H., Grabowski E.J.J., Karady S., Ryan K.M., and Weinstock W.M. Angew. Chem., Int. Ed. Engl. 25 (1986) 476-477
32. Conn R.S.E., Lovell A.V., Karady S., and Weinstock L.M. J. Org. Chem. 51 (1986) 4710-4711
33. Hughes D.L., Dolling U.-H., Ryan K.M., Schoenewaldt E.F., and Grabowski E.J.J. J. Org. Chem. 52 (1987) 4745-4752
34. Anelli P.L., Biffi C., Montanari F., and Quici S. J. Org. Chem. 52 (1987) 2559-2562
35. For a review, see:. Rickborn B. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 3 (1991), Pergamon, Oxford 721-732
36. Kolb H.C., VanNieuwenhze M.S., and Sharpless K.B. Chem. Rev. 94 (1994) 2483-2547
37. Marshall J.A., and Hinkle K.W. J. Org. Chem. 60 (1995) 1920-1921
38. Miyai T., Inoue K., Yasuda M., and Baba A. Synlett (1997) 699-700
39. Burns N.Z., Baran P.S., and Hoffmann R.W. Angew. Chem., Int. Ed. 48 (2009) 2854-2867
40. Burns, N. Z.; Krylova, I. N.; Hannoush, R. N.; Baran, P. S. J. Am. Chem. Soc., in press. doi:10.1021/ja903745s.