Hybrids of sugars and aromatics: A Pd-catalyzed modular approach to chromans and isochromans

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 11, 2010, Pages 3656-3667

  Leibeling, Markus ^a   Koester, Dennis C ^a   Pawliczek, Martin ^a   Kratzert, Daniel ^a   Dittrich, Birger ^a   Werz, Daniel B ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Carbohydrates; Chromans; Domino reactions; Isochromans; Palladium

Indexed keywords

ALKYNE DERIVATIVE; AROMATIC COMPOUND; BENZENE; CARBOHYDRATE; CHROMAN DERIVATIVE; ISOCHROMAN DERIVATIVE; ISOTOPE; PALLADIUM;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CYCLIZATION; ISOTOPE LABELING; OXIDATION; SYNTHESIS;

CARBOHYDRATES; CATALYSIS; CHROMANS; HYDROCARBONS, AROMATIC; ISOTOPE LABELING; PALLADIUM; SMALL MOLECULE LIBRARIES;

EID: 77953232561     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.03.004     Document Type: Article

References (88)

1. Ellis G.P., and Lockhart I.M. The Chemistry of Heterocyclic Compounds, Chromenes, Chromanones and Chromones (2007), Wiley-VCH, New York
2. Nicolaou K.C., Pfefferkorn J.A., Barluenga S., Mitchell H.J., Roecker A.J., and Cao G.-Q. J. Am. Chem. Soc. 122 (2000) 9968-9976
3. Evans H.M., and Bishop K.S. Science 56 (1929) 650-651
4. Tietze L.F., Stecker F., Zinngrebe J., and Sommer K.M. Chem. Eur. J. 12 (2006) 8770-8776
5. Chapelat J., Buss A., Chougnet A., and Woggon W.-D. Org. Lett. 10 (2008) 5123-5126
6. Liu K., Chougnet A., and Woggon W.-D. Angew. Chem. 120 (2008) 5911-5913 Angew. Chem., Int. Ed. 2008, 47, 5827-5829
7. Ashwood V.A., Buckingham R.E., Cassidy F., Evans J.M., Faruk E.A., Hamilton T.C., Nash D.J., Stemp G., and Willcocks K. J. Med. Chem. 29 (1986) 2194-2201
8. Yu S.P., Yeh C.-H., Sensi S.L., Gwag B.J., Canzoniero L.M.T., Farhangrazi Z.S., Ying H.S., Tian M., Dugan L.L., and Choi D.W. Science 278 (1997) 114-117
9. Kurdyumov A.V., Hsung R.P., Ihlen K., and Wang J. Org. Lett. 5 (2003) 3935-3938
10. Kang Y., Mei Y., Du Y., and Jin Z. Org. Lett. 5 (2003) 4481-4484
11. For recent approaches leading to chroman, chromen, isochroman and isochromen skeletons, see:. Hong L., Wang L., Sun W., Wong K., and Wang R. J. Org. Chem. 74 (2009) 6881-6884
12. Shen H.C. Tetrahedron 65 (2009) 3931-3952
13. Varela-Fernández A., González-Rodríguez C., Varela J.A., Castedo L., and Saá C. Org. Lett. 11 (2009) 5350-5353
14. Meng X., Huang Y., Zhao H., Xie P., Ma J., and Chen R. Org. Lett. 11 (2009) 991-994
15. Marsini M.A., Huang Y., Lindsey C.C., Wu K.-L., and Pettus T.R.R. Org. Lett. 10 (2008) 1477-1480
16. Saito N., Ryoda A., Nakanishi W., Kumamoto T., and Ishikawa T. Eur. J. Org. Chem. (2008) 2759-2766
17. Fukamizu K., Miyake Y., and Nishibayashi Y. J. Am. Chem. Soc. 130 (2008) 10498-10499
18. Hashmi A.S.K., Rudolph M., Bats J.W., Frey W., Rominger F., and Oeser T. Chem. Eur. J. 14 (2008) 6672-6678
19. Wegner H.A., Ahles S., and Neuburger M. Chem. Eur. J. 14 (2008) 11310-11313
20. Gérard E.M.C., and Bräse S. Chem. Eur. J. 14 (2008) 8086-8089
21. Shi Y.-L., and Shi M. Org. Biomol. Chem. 5 (2007) 1499-1504
22. Houpis I.N., van Hoeck J.-P., and Tilstam U. Synlett (2007) 2179-2184
23. Hashmi A.S.K., Wölfle M., Ata F., Hamzic M., Salathé R., and Frey W. Adv. Synth. Catal. 348 (2006) 2501-2508
24. de Koning C.B., Giles R.G.F., Green I.R., and Jahed N.M. Tetrahedron 60 (2004) 2629-2637
25. van Lingen H.L., Zhuang W., Hansen T., Rutjes F.P.J.T., and Jørgensen K.A. Org. Biomol. Chem. 1 (2003) 1953-1958
26. Wang Q., and Finn M.G. Org. Lett. 2 (2000) 4063-4065
27. Chang S., and Grubbs R.H. J. Org. Chem. 63 (1998) 864-866
28. Tietze L.F., Burkhardt O., and Henrich M. Liebigs Ann./Recl. (1997) 887-891
29. Zu L., Zhang S., Xie H., and Wang W. Org. Lett. 11 (2009) 1627-1630
30. Yamamoto Y., and Itonaga K. Org. Lett. 11 (2009) 717-720
31. Trost B.M., and Crawley M.L. Chem. Rev. 103 (2003) 2921-2944
32. Trost B.M. Chem. Pharm. Bull. 50 (2002) 1-14
33. Helmchen G., and Pfaltz A. Acc. Chem. Res. 33 (2000) 336-345
34. Trost B.M., Shen H.C., Dong L., Surivet J.-P., and Sylvain C. J. Am. Chem. Soc. 126 (2004) 11966-11983
35. Murphy P.V. Eur. J. Org. Chem. 25 (2007) 4177-4187
36. Abrous L., Jokiel P.A., Friedrich S.R., Hynes Jr. J., Smith III A.B., and Hirschmann R. J. Org. Chem. 69 (2004) 280-302
37. Brand C., Rauch G., Zanoni M., Dittrich B., and Werz D.B. J. Org. Chem. 74 (2009) 8779-8786
38. Holkenbrink A., Vicente J.B., and Werz D.B. Synthesis (2009) 2596-2604
39. Peri F., Airoldi C., Colombo S., Mari S., Jiménez-Barbero J., Martegani E., and Nicotra F. Eur. J. Org. Chem. (2006) 3707-3720
40. Fragai M., Nativi C., Richichi B., and Venturi C. ChemBioChem 6 (2005) 1345-1349
41. Capozzi G., Giannini S., Menichetti S., Nativi C., Giolitti A., Patacchini R., Perrotta E., Altamura M., and Maggi C.A. Bioorg. Med. Chem. Lett. 12 (2002) 2263-2266
42. Leibeling M., Koester D.C., Pawliczek M., Schild S.C., and Werz D.B. Nat. Chem. Biol. 6 (2010) 199-201
43. Young D.W. Nat. Chem. Biol. 6 (2010) 174-175
44. Tietze L.F., Brasche G., and Gericke K.M. Domino Reactions in Organic Synthesis (2006), Wiley-VCH, Weinheim
45. Cui S.-L., Wang J., and Wang Y.-G. J. Am. Chem. Soc. 130 (2008) 13526-13527
46. Blond G., Bour C., Salem B., and Suffert J. Org. Lett. 10 (2008) 1075-1078
47. Pinto A., Neuville L., and Zhu J. Angew. Chem. 119 (2007) 3355-3359 Angew. Chem., Int. Ed. 2007, 46, 3291-3295
48. Dong C.-G., Yeung P., and Hu Q.-S. Org. Lett. 9 (2007) 363-366
49. Pinto A., Neuville L., Retailleau P., and Zhu J. Org. Lett. 8 (2006) 4927-4930
50. Enders D., Huttl M.R.M., Grondal C., and Raabe G. Nature 441 (2006) 861-863
51. Salem B., and Suffert J. Angew. Chem. 116 (2004) 2886-2890 Angew. Chem., Int. Ed. 2004, 43, 2826-2830
52. Salem B., Klotz P., and Suffert J. Synthesis 2 (2004) 298-307
53. Salem B., Klotz P., and Suffert J. Org. Lett. 5 (2003) 845-848
54. Suffert J., Salem B., and Klotz P. J. Am. Chem. Soc. 123 (2001) 12107-12108
55. Tietze L.F. Chem. Rev. 96 (1996) 115-136
56. Tietze L.F., and Beifuss U. Angew. Chem. 105 (1993) 137-170 Angew. Chem., Int. Ed. Engl. 1993, 32, 131-163
57. Negishi E., Harring L.S., Owczarczyk Z., Mohamud M.M., and Ay M. Tetrahedron Lett. 33 (1992) 3253-3256
58. Meyer F.E., and de Meijere A. Synlett (1991) 777-778
59. Yoshimoto K., Kawabata H., Nakamichi N., and Hayashi M. Chem. Lett. 30 (2001) 934-935
60. Harada H., Thalji R.K., Bergman R.G., and Ellman J.A. J. Org. Chem. 73 (2008) 6772-6779
61. Karrer P., Becker B., Benz F., Frei P., Salomon H., and Schöpp K. Helv. Chim. Acta 18 (1935) 1435-1448
62. Walker II J.A., Chem J.J., Wise D.S., and Townsend L.B. J. Org. Chem. 61 (1996) 2219-2221
63. Ireland R.E., Wilcox C.S., and Thaisrivongs S. J. Org. Chem. 43 (1978) 786-787
64. Mukai C., Nomura I., and Kitagaki S. J. Org. Chem. 68 (2003) 1376-1385
65. Li M., and O'Doherty G.A. Org. Lett. 8 (2006) 6087-6090
66. Fleming I., Henning R., Parker D.C., Plaut H.E., and Sanderson P.E.J. J. Chem. Soc., Perkin Trans. 1 (1995) 317-337
67. Tamao K., and Kumada M. Tetrahedron Lett. 25 (1984) 321-324
68. Pyridine moieties were built up via Co-mediated cyclizations, e.g.:. Zhou Y., Porco Jr. J.A., and Snyder J.K. Org. Lett. 9 (2007) 393-396
69. Pd-catalyzed reactions, e.g.:. Yang C.-C., Sun P.-J., and Fang J.-M. J. Chem. Soc., Chem. Commun. (1994) 2629-2630
70. Yang C.-C., Tai H.-M., and Sun P.-J. J. Chem. Soc., Perkin Trans. 1 (1997) 2843-2850
71. Tsuji J., Watanabe H., Minami I., and Shimizu I. J. Am. Chem. Soc. 107 (1985) 2196-2198
72. Ferrier R.J., Overend W.G., and Ryan A.E. J. Chem. Soc. (1962) 3667-3670
73. Durham T.B., and Miller M.J. Org. Lett. 4 (2002) 135-138
74. Agarval A., Rani S., and Vankar Y.D. J. Org. Chem. 69 (2004) 6137-6140
75. Bondi A. J. Phys. Chem. 68 (1964) 441-451
76. Ramasubbu N., Parthasarathy R., and Murray-Rust P. J. Am. Chem. Soc. 108 (1986) 4308-4314
77. Desiraju G.R., and Parthasarathy R. J. Am. Chem. Soc. 111 (1989) 8725-8726
78. Metrangolo P., Meyer F., Pilati T., Resnati G., and Terraneo G. Angew. Chem. 120 (2008) 6206-6220 Angew. Chem., Int. Ed. 2008, 47, 6114-6127
79. Esser B., Bandyopadhyay A., Rominger F., and Gleiter R. Chem. Eur. J. 15 (2009) 3368-3379
80. Pyykkö P. Chem. Rev. 97 (1997) 597-636
81. Bleiholder C., Werz D.B., Köppel H., and Gleiter R. J. Am. Chem. Soc. 128 (2006) 2666-2674
82. Bleiholder C., Gleiter R., Werz D.B., and Köppel H. Inorg. Chem. 46 (2007) 2249-2260
83. Agnihotri G., and Misra A.K. Tetrahedron Lett. 47 (2006) 3653-3658
84. Kottke T., and Stalke D. J. Appl. Crystallogr. 26 (1993) 615-619
85. Bruker, saint v7.34A., Bruker AXS Inc., Madison (WI, USA), 2005.
86. Sheldrick, G. M. sadabs 2008/1, Göttingen, 2008.
87. Sheldrick G.M. Acta Crystallogr., Sect. A 64 (2008) 112-122
88. Flack H.D. Acta Crystallogr., Sect. A 39 (1983) 876-881