Studies on the Claisen rearrangements in the indolo[2,3-b]quinoline system

Organic and Biomolecular Chemistry

Volumn 8, Issue 2, 2010, Pages 442-450

  Voûte, Nicholas ^a   Philp, Douglas ^a   Slawin, Alexandra M Z ^a   Westwood, Nicholas J ^a  

^a UNIVERSITY OF ST ANDREWS   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CLAISEN REARRANGEMENT; DFT CALCULATION; NATURAL PRODUCTS; RATIONALISATION; SUBSTRATE STRUCTURE;

SULFUR COMPOUNDS;

ETHERS;

BIOLOGICAL PRODUCT; INDOLE DERIVATIVE; QUINOLINE DERIVATIVE;

ARTICLE; CHEMISTRY; QUANTUM THEORY; SYNTHESIS; THERMODYNAMICS;

BIOLOGICAL PRODUCTS; INDOLES; QUANTUM THEORY; QUINOLINES; THERMODYNAMICS;

EID: 72949119693     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b915677a     Document Type: Article

References (54)

1. K. Fuji Chem. Rev. 1993 93 2037 2066
2. J. Christoffers A. Mann Angew. Chem., Int. Ed. 2001 40 4591 4597
3. I. Denissova L. Barriault Tetrahedron 2003 59 10105 10146
4. E. A. Peterson L. E. Overman Proc. Natl. Acad. Sci. U. S. A. 2004 101 11943 11948
5. J. Christoffers A. Bravo Adv. Synth. Catal. 2005 347 1473 1482
6. A. M. M. Castro Chem. Rev. 2004 104 2939 3002
7. For a recent review of the Claisen rearrangement see: T. Kawasaki M. Shinada D. Kamimura M. Ohzono A. Ogawa Chem. Commun. 2006 420 422
8. T. Kawasaki A. Ogawa R. Terashima T. Saheki N. Ban H. Sekiguchi K. Sakaguchi M. Sakamoto J. Org. Chem. 2005 70 2957 2966
9. T. Kawasaki A. Ogawa Y. Takashima M. Sakamoto Tetrahedron Lett. 2003 44 1591 1593
10. T. Kawasaki R. Terashima K. Sakaguchi H. Sekiguchi M. Sakamoto Tetrahedron Lett. 1996 37 7525 7524
11. H. Miyamoto Y. Okawa A. Nakazaki S. Kobayashi Angew. Chem., Int. Ed. 2006 45 2274 2277
12. A. Nakazaki H. Miyamoto K. Henmi S. Kobayashi Synlett 2005 9 1417 1420
13. K. I. Booker-Milburn M. Fedouloff S. Paknoham J. Strachan J. Melville M. Voyle Tetrahedron Lett. 2000 41 4657 4661
14. B. J. Newhouse J. Bordner D. J. Augeri C. S. Litts E. F. Keinman J. Org. Chem. 1992 57 6991 6995
15. S. Kotha K. Mandal Tetrahedron Lett. 2004 45 1391 1394
16. A. Numata C. Takahashi I. Yoshinori T. Takada K. Kawai U. Yoshihide E. Matsumura M. Imachi T. Ito T. Hasegawa Tetrahedron Lett. 1993 34 2355 2358
17. R. Jadulco R. A. Edrada R. Ebel A. Berg K. Schaumann V. Wray K. Stube P. Proksch J. Nat. Prod. 2004 67 78 81
18. H. Hayashi H. Matsumoto K. Akiyama Biosci., Biotechnol., Biochem. 2004 68 753 756
19. B. Andersen J. Smedsgaard J. C. Frisvad J. Agric. Food Chem. 2004 52 2421 2428
20. P. W. Dalsgaard J. W. Blunt M. H. G. Munro J. C. Frisvad C. Christopers J. Nat. Prod. 2005 68 258 261
21. J. Bergman R. Engqvist C. Stålhandske H. Wallberg Tetrahedron 2003 59 1033 1048
22. For a more detailed discussion see the ESI S. Hoops S. Sahle R. Gauges C. Lee J. Pahle N. Simus M. Singhal L. Xu P. Mendes U. Kummer Bioinformatics 2006 22 3067 3074
23. 13C signal could correspond to the carbonyl carbon of the structure below. Whilst this cannot be ruled out without synthesis of this compound, initial computational studies using the Database Service suggest that the carbonyl carbon in 5 would be expected to come at some 17 ppm downfield of that for the structure below;
24. D. A. Fletcher R. F. McMecking D. Parkin J. Chem. Inf. Comput. Sci. 1996 36 746 749
25. H.Y. Yoo K. N. Houk J. Am. Chem. Soc. 1997 119 2877 2884, and references therein
26. 2 = 0.1376 for all data. Flack parameter -0.005(14)
27. G. M. Coppola J. Heterocycl. Chem. 1980 17 1785 1787
28. J. Bergman U. Tilstam K. W. Toernroos J. Chem. Soc., Perkin Trans. 1 1987 519 527
29. D. P. Curran Y. G. Suh J. Am. Chem. Soc. 1984 106 5002 5004
30. J. J. Gajewski N. D. Conrad J. Am. Chem. Soc. 1979 101 2747 2748
31. K. D. McMichael G. L. Korver J. Am. Chem. Soc. 1979 101 2746 2747
32. Limited information on the absolute stereochemistry of the communesin group of natural products is available and is confused by previous structural corrections. As (R)-(-)-3-buten-2-ol is also readily available, 18 can be prepared as either enantiomer as required. An elegant palladium-catalyzed enantioselective allylation has been used to generate the C11a quaternary centre in systems of this type.
33. B. M. Trost J. Quancard J. Am. Chem. Soc. 2006 128 6314 6315
34. For an overview of asymmetric Claisen reactions see: D. Enders M. Knopp R. Schiffers Tetrahedron: Asymmetry 1996 7 1847 1882
35. H. Ito T. Taguchi Chem. Soc. Rev. 1999 28 43 50
36. B. M. Trost G. Dong J. A. Vance J. Am. Chem. Soc. 2007 129 4540 4541
37. For existing approaches to the communesins see: J. Yang H. Wu L. Shen Y. Qin J. Am. Chem. Soc. 2007 129 13794 13795
38. J. A. May R. K. Zeidan B. M. Stoltz Tetrahedron Lett. 2003 44 1203 1205
39. J.A. May B. Stoltz Tetrahedron 2006 62 5262 5271
40. S. L. Crawley R. L. Funk Org. Lett. 2003 5 3169 3171
41. S. L. Crawley R. L. Funk Org. Lett. 2006 8 3995 3998
42. J. Yang H. Song X. Xiao J. Wang Y. Qin Org. Lett. 2006 8 2187 2190
43. J. H. Seo G. D. Artman III S. M. Weinreb J. Org. Chem. 2006 71 8891 8900
44. J. H. George R. M. Adlington Synlett 2008 14 2093 2096
45. J. B. Hendrickson R. Rees R. Goschke Proc. Chem. Soc. 1962 383 384
46. The synthesis of the structurally related natural product, perophoramidine and its dehalo-analogue have also been reported recently: J. R. Fuchs R. L. Funk J. Am. Chem. Soc. 2004 126 5068 5069
47. A. Sabahi A. Novikov J. D. Rainier Angew. Chem., Int. Ed. 2006 45 4317 4320
48. 4-Bromoindole derivative 20 was initially prepared according to: M. Somei K. Kizu M. Kunimoto F. Yamada Chem. Pharm. Bull. 1985 33 3696 3708
49. F. Yamada M. Somei Heterocycles 1987 26 1173 1176
50. E. C. Taylor F. Kienzle R. L. Robey A. McKillop J. D. Hunt J. Am. Chem. Soc. 1971 93 4845 4850
51. Y. Gao J. M. Klunder R. M. Hanson H. Masamune S. Y. Ko K. B. Sharpless J. Am. Chem. Soc. 1987 109 5765 5780
52. E. Balmer A. Germain W. P. Jackson B. Lygo J. Chem. Soc., Perkin Trans. 1 1993 399 400
53. As determined by Mosher's ester formation: J. A. Dale H. S. Mosher J. Am. Chem. Soc. 1973 95 512 519
54. R. R. Fraser M. A. Petit J. K. Saunders J. Chem. Soc., Chem. Commun. 1971 1450 1451