The absolute axial configurations of knipholone and knipholone anthrone by TDDFT and DFT/MRCI CD calculations: a revision

Tetrahedron

Volumn 63, Issue 39, 2007, Pages 9810-9824

  Bringmann, Gerhard ^a   Maksimenka, Katja ^a   Mutanyatta Comar, Joan ^a   Knauer, Michael ^a   Bruhn, Torsten ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

Absolute configuration; Axial chirality; Knipholone; Knipholone anthrone; Quantum chemical CD calculations

Indexed keywords

ANTHRAQUINONE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CIRCULAR DICHROISM; CONFORMATIONAL TRANSITION; DENSITY FUNCTIONAL THEORY; ENANTIOMER; MOLECULAR INTERACTION; PRIORITY JOURNAL; QUANTUM CHEMISTRY; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 34547734417     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.07.001     Document Type: Article

References (69)

1. Dagne E., and Steglich W. Phytochemistry 23 (1984) 1729-1731
2. Dagne E., and Yenesew A. Phytochemistry 34 (1993) 1440-1441
3. Bringmann G., Noll T.F., Gulder T., Dreyer M., Grüne M., and Moskau D. J. Org. Chem. 72 (2007) 3247-3252
4. Bringmann G., Menche D., Bezabih M., Abegaz B.M., and Kaminsky R. Planta Med. 65 (1999) 757-758
5. Kuroda M., Mimaki Y., Sakagami H., and Sashida Y. J. Nat. Prod. 66 (2003) 894-897
6. Habtemariam S. Food Chem. 102 (2007) 1042-1047
7. Wube A.A., Bucar F., Asres K., Gibbons S., Adams M., Streit B., Bodensieck A., and Bauer R. Phytomedicine 13 (2006) 452-456
8. Bringmann G., Günther C., Ochse M., Schupp O., and Tasler S. In: Herz W., Falk H., Kirby G.W., and Moore R.E. (Eds). Progress in the Chemistry of Organic Natural Products Vol. 82 (2001), Springer, Vienna 1-249
9. Mutanyatta J., Bezabih M., Abegaz B.M., Dreyer M., Brun R., Kocher N., and Bringmann G. Tetrahedron 61 (2005) 8475-8484
10. Bringmann G., Kraus J., Menche D., and Messer K. Tetrahedron 55 (1999) 7563-7572
11. Bringmann G., and Menche D. Angew. Chem., Int. Ed. 40 (2001) 1687-1690
12. Bringmann G., Menche D., Kraus J., Mühlbacher J., Peters K., Peters E.-M., Brun R., Bezabih M., and Abegaz B.M. J. Org. Chem. 67 (2002) 5595-5610
13. Bringmann G., Breuning M., and Tasler S. Synthesis (1999) 525-558
14. Bringmann G., Breuning M., Pfeifer R.-M., Schenk W.A., Kamikawa K., and Uemura M. J. Organomet. Chem. 661 (2002) 31-47
15. Bringmann G., Pabst T., Henschel P., Kraus J., Peters K., Peters E.-M., Rycroft D.S., and Connolly J.D. J. Am. Chem. Soc. 122 (2000) 9127-9133
16. Bringmann G., Menche D., Mühlbacher J., Reichert M., Saito N., Pfeiffer S.S., and Lipshutz B.H. Org. Lett. 4 (2002) 2833-2836
17. Bringmann G., Saeb W., and Rübenacker M. Tetrahedron 55 (1999) 423-432
18. Bringmann G., Ochse M., and Götz R. J. Org. Chem. 65 (2000) 2069-2077
19. Bringmann G., and Menche D. Acc. Chem. Res. 34 (2001) 615-624
20. Bringmann G., Tasler S., Pfeifer R.-M., and Breuning M. J. Organomet. Chem. 661 (2002) 49-65
21. Abe H., Takeda S., Fujita T., Nishioka K., Takeuchi Y., and Harayama T. Tetrahedron Lett. 45 (2004) 2327-2329
22. Fletcher S.P., Dumur F., Pollard M.M., and Feringa B.L. Science 310 (2005) 80-82
23. Takeda S., Abe H., Takeuchi Y., and Harayama T. Tetrahedron 63 (2006) 396-408
24. Bringmann G., Pfeifer R.-M., Schreiber P., Hartner K., Schraut M., and Breuning M. Tetrahedron 60 (2004) 4349-4360
25. Ohmori K., Tamiya M., Kitamura M., Kato H., Oorui M., and Suzuki K. Angew. Chem., Int. Ed. 44 (2005) 3871-3874
26. Bringmann G., and Vitt D. J. Org. Chem. 60 (1995) 7674-7681
27. Yenesew, A.; Wanjohi, J. M.; Midiwo, J. O.; Heydenreich, M.; Peter, M. G.; Brun, R.; Müller, W. E. G.; Maksimenka, K.; Mutanyatta-Comar, J.; Bringmann, G. Unpublished results.
28. Doub L., and Vandenbelt J.M. J. Am. Chem. Soc. 69 (1947) 2714-2723
29. Shimada R., and Goodman L. J. Chem. Phys. 43 (1965) 2027-2041
30. Dehler J., and Dörr F. Tetrahedron Lett. 6 (1965) 2155-2160
31. Harada N., and Nakanishi K. Acc. Chem. Res. 5 (1972) 257-263
32. Casida M.E. In: Chong D.P. (Ed). Recent Advances in Density Functional Methods (1995), World Scientific, Singapore 155-192
33. Gross E.K.U., Dobson J.F., and Petersilka M. Top. Curr. Chem. 181 (1996) 80-172
34. Furche F., Ahlrichs R., Wachsmann C., Weber E., Sobanski A., Vögtle F., and Grimme S. J. Am. Chem. Soc. 122 (2000) 1717-1724
35. Crawford T.D. Theor. Chem. Acc. 115 (2006) 227-245
36. Grimme S., and Waletzke M. J. Chem. Phys. 111 (1999) 5645-5655
37. Stewart J.J.P. J. Comput. Chem. 10 (1989) 221-264
38. Vahtras O., Almloef J., and Feyereisen M.W. Chem. Phys. Lett. 213 (1993) 514-518
39. Becke A.D. Phys. Rev. A 38 (1988) 3098-3100
40. Lee C., Yang W., and Parr R.G. Phys. Rev. B 37 (1988) 785-789
41. Bauernschmitt R., Häser M., Treutler O., and Ahlrichs R. Chem. Phys. Lett. 264 (1997) 573-578
42. Koch W., and Holthausen M.C. A Chemist's Guide to Density Functional Theory. 2nd ed. (2001), Wiley-VCH-GmbH, Weinheim
43. Becke A.D. J. Chem. Phys. 98 (1993) 5648-5652
44. Schäfer A., Huber C., and Ahlrichs R. J. Chem. Phys. 100 (1994) 5829-5835
45. Becke A.D. J. Chem. Phys. 98 (1993) 1372-1377
46. Diedrich C., and Grimme S. J. Phys. Chem. A 107 (2003) 2524-2539
47. Bringmann G., and Busemann S. In: Schreier P., Herderich M., Humpf H.-U., and Schwab W. (Eds). Natural Product Analysis: Chromatography, Spectroscopy, Biological Testing (1998), Vieweg, Wiesbaden 195-211
48. Bezabih M., Motlhagodi S., and Abegaz B.M. Phytochemistry 46 (1997) 1063-1067
49. Abegaz B.M., Bezabih M., Msuta T., Brun R., Menche D., Mühlbacher J., and Bringmann G. J. Nat. Prod. 65 (2002) 1117-1121
50. Hui C.W., Mak T.C.W., and Wong H.N.C. Tetrahedron 60 (2004) 3523-3531
51. Lu L., Chen Q., Zhu X., and Chen C. Synthesis (2003) 2464-2466
52. Tius M.A., Gomez-Galeno J., Gu X.-Q., and Zaidi J.H. J. Am. Chem. Soc. 113 (1991) 5775-5783
53. Quast H., and Fuchsbauer H.-L. Chem. Ber. 119 (1986) 1016-1038
54. Kraus G.A., and Man T.O. Synth. Commun. 16 (1986) 1037-1042
55. Krohn K., and Miehe F. Liebigs Ann. Chem. (1985) 1329-1335
56. Winters R.T., Sercel A.D., and Showalter H.D.H. Synthesis (1998) 712-714
57. Bringmann G., Rübenacker M., Jansen J.R., and Scheutzow D. Tetrahedron Lett. 31 (1990) 639-642
58. Müller M., Lamottke K., Steglich W., Busemann S., Reichert M., Bringmann G., and Spiteller P. Eur. J. Org. Chem. (2004) 4850-4855
59. 9
60. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery J.J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. GAUSSIAN 03, Revision D.02 (2004), Gaussian, Wallingford, CT
61. Clark M., Cramer III R.D., and Van Opdenbosch N. J. Comput. Chem. 10 (1989) 982-1012
62. SYBYL; Tripos Associates: 1699 St. Hanley Road, Suite 303, St. Louis, MO 63144, USA, 2006.
63. Ahlrichs R., Bär M., Baron H.-P., Bauernschmitt R., Böcker S., Crawford N., Deglmann P., Ehrig M., Eichkorn K., Elliott S., Furche F., Haase F., Häser M., Horn H., Hättig C., Huber C., Huniar U., Kattannek M., Köhn A., Kölmel C., Kollwitz M., May K., Nava P., Ochsenfeld C., Öhm H., Patzelt H., Rappoport O., Rubner O., Schäfer A., Schneider U., Sierka M., Treutler O., Unterreiner B., Arnim M.v., Weigend F., Weis P., and Weiss H. TURBOMOLE 5.8 ed. (2005), Universität Karlsruhe, Karlsruhe, Germany
64. Harris R.A. J. Chem. Phys. 50 (1969) 3947-3951
65. Schellman J.A. Chem. Rev. 75 (1975) 323-331
66. Auterhoff H., and Scherff F.C. Arch. Pharm. 293 (1969) 918-925
67. Bringmann G., Menche D., Brun R., Msuta T., and Abegaz B.M. Eur. J. Org. Chem. (2002) 1107-1111
68. Qhotsokoane-Lusunzi M.A., and Karuso P. Aust. J. Chem. 54 (2001) 427-430
69. Qhotsokoane-Lusunzi M.A., and Karuso P. J. Nat. Prod. 64 (2001) 1368-1372 Note that the structures 1 and 2 must be interchanged in this article!