Simple circular dichroic method for the determination of absolute configuration of 5-substituted 2(5H)-furanones

Journal of Organic Chemistry

Volumn 61, Issue 4, 1996, Pages 1513-1515

  Gawronski, Jacek K ^a   Van Oeveren, Arjan ^b   Van Der Deen, Hanncke ^b   Leung, Chiu W ^b   Feringa, Ben L ^b  

^a ADAM MICKIEWICZ UNIVERSITY   (Poland)

^b UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

2 FURANONE DERIVATIVE;

ARTICLE; CIRCULAR DICHROISM; DRUG STRUCTURE;

EID: 0029958759     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951400l     Document Type: Article

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46. Examples of X-ray structure determination of butenolides: (a) Coggon, P.; Luhan, P. A.; McPhail, A. T. J. Chem. Soc. Perkin Trans. 2 1973, 465. (b) Ružić-Toroš, Ž.; Kojić-Prodić, B. Acta Crystallogr. 1976, B32, 2333. (c) Ružić-Toroš, Ž.; Lazarini, F. Ibid. 1978, B34, 854. (d) Ružić-Toroš, Z.; Leban, I. Ibid. 1978, B34, 1226. (e) Ružić-Toroš, Z.; Kojić-Prodić, B. Ibid. 1982, B38, 1664. (f) Parvez, M.; Fajardo, V.; Shamma, M. ibid. 1988, C44, 553. (g) Font, J.; Sanchez-Ferrando, F.; Segura, C.; Piniella, J. F.; Jeffrey, G. A.; Ruble, J. R. J. Heterocycl. Chem. 1990, 27, 183. (h) Ammon, H. L.; DeShong, P.; Lessen, T. A. Acta Crystallogr. 1991, C47, 2488. (i) Hynes, R. C. Ibid. 1992, C48, 395. (j) Linden, A. Ibid. 1992, C48, 1514. (k) Parvez, M.; Yu, S.; Keay, B. A. Ibid. 1993, C49, 992.
47. Examples of X-ray structure determination of butenolides: (a) Coggon, P.; Luhan, P. A.; McPhail, A. T. J. Chem. Soc. Perkin Trans. 2 1973, 465. (b) Ružić-Toroš, Ž.; Kojić-Prodić, B. Acta Crystallogr. 1976, B32, 2333. (c) Ružić-Toroš, Ž.; Lazarini, F. Ibid. 1978, B34, 854. (d) Ružić-Toroš, Z.; Leban, I. Ibid. 1978, B34, 1226. (e) Ružić-Toroš, Z.; Kojić-Prodić, B. Ibid. 1982, B38, 1664. (f) Parvez, M.; Fajardo, V.; Shamma, M. ibid. 1988, C44, 553. (g) Font, J.; Sanchez-Ferrando, F.; Segura, C.; Piniella, J. F.; Jeffrey, G. A.; Ruble, J. R. J. Heterocycl. Chem. 1990, 27, 183. (h) Ammon, H. L.; DeShong, P.; Lessen, T. A. Acta Crystallogr. 1991, C47, 2488. (i) Hynes, R. C. Ibid. 1992, C48, 395. (j) Linden, A. Ibid. 1992, C48, 1514. (k) Parvez, M.; Yu, S.; Keay, B. A. Ibid. 1993, C49, 992.
48. Examples of X-ray structure determination of butenolides: (a) Coggon, P.; Luhan, P. A.; McPhail, A. T. J. Chem. Soc. Perkin Trans. 2 1973, 465. (b) Ružić-Toroš, Ž.; Kojić-Prodić, B. Acta Crystallogr. 1976, B32, 2333. (c) Ružić-Toroš, Ž.; Lazarini, F. Ibid. 1978, B34, 854. (d) Ružić-Toroš, Z.; Leban, I. Ibid. 1978, B34, 1226. (e) Ružić-Toroš, Z.; Kojić-Prodić, B. Ibid. 1982, B38, 1664. (f) Parvez, M.; Fajardo, V.; Shamma, M. ibid. 1988, C44, 553. (g) Font, J.; Sanchez-Ferrando, F.; Segura, C.; Piniella, J. F.; Jeffrey, G. A.; Ruble, J. R. J. Heterocycl. Chem. 1990, 27, 183. (h) Ammon, H. L.; DeShong, P.; Lessen, T. A. Acta Crystallogr. 1991, C47, 2488. (i) Hynes, R. C. Ibid. 1992, C48, 395. (j) Linden, A. Ibid. 1992, C48, 1514. (k) Parvez, M.; Yu, S.; Keay, B. A. Ibid. 1993, C49, 992.
49. Examples of X-ray structure determination of butenolides: (a) Coggon, P.; Luhan, P. A.; McPhail, A. T. J. Chem. Soc. Perkin Trans. 2 1973, 465. (b) Ružić-Toroš, Ž.; Kojić-Prodić, B. Acta Crystallogr. 1976, B32, 2333. (c) Ružić-Toroš, Ž.; Lazarini, F. Ibid. 1978, B34, 854. (d) Ružić-Toroš, Z.; Leban, I. Ibid. 1978, B34, 1226. (e) Ružić-Toroš, Z.; Kojić-Prodić, B. Ibid. 1982, B38, 1664. (f) Parvez, M.; Fajardo, V.; Shamma, M. ibid. 1988, C44, 553. (g) Font, J.; Sanchez-Ferrando, F.; Segura, C.; Piniella, J. F.; Jeffrey, G. A.; Ruble, J. R. J. Heterocycl. Chem. 1990, 27, 183. (h) Ammon, H. L.; DeShong, P.; Lessen, T. A. Acta Crystallogr. 1991, C47, 2488. (i) Hynes, R. C. Ibid. 1992, C48, 395. (j) Linden, A. Ibid. 1992, C48, 1514. (k) Parvez, M.; Yu, S.; Keay, B. A. Ibid. 1993, C49, 992.
50. Examples of X-ray structure determination of butenolides: (a) Coggon, P.; Luhan, P. A.; McPhail, A. T. J. Chem. Soc. Perkin Trans. 2 1973, 465. (b) Ružić-Toroš, Ž.; Kojić-Prodić, B. Acta Crystallogr. 1976, B32, 2333. (c) Ružić-Toroš, Ž.; Lazarini, F. Ibid. 1978, B34, 854. (d) Ružić-Toroš, Z.; Leban, I. Ibid. 1978, B34, 1226. (e) Ružić-Toroš, Z.; Kojić-Prodić, B. Ibid. 1982, B38, 1664. (f) Parvez, M.; Fajardo, V.; Shamma, M. ibid. 1988, C44, 553. (g) Font, J.; Sanchez-Ferrando, F.; Segura, C.; Piniella, J. F.; Jeffrey, G. A.; Ruble, J. R. J. Heterocycl. Chem. 1990, 27, 183. (h) Ammon, H. L.; DeShong, P.; Lessen, T. A. Acta Crystallogr. 1991, C47, 2488. (i) Hynes, R. C. Ibid. 1992, C48, 395. (j) Linden, A. Ibid. 1992, C48, 1514. (k) Parvez, M.; Yu, S.; Keay, B. A. Ibid. 1993, C49, 992.
51. Examples of X-ray structure determination of butenolides: (a) Coggon, P.; Luhan, P. A.; McPhail, A. T. J. Chem. Soc. Perkin Trans. 2 1973, 465. (b) Ružić-Toroš, Ž.; Kojić-Prodić, B. Acta Crystallogr. 1976, B32, 2333. (c) Ružić-Toroš, Ž.; Lazarini, F. Ibid. 1978, B34, 854. (d) Ružić-Toroš, Z.; Leban, I. Ibid. 1978, B34, 1226. (e) Ružić-Toroš, Z.; Kojić-Prodić, B. Ibid. 1982, B38, 1664. (f) Parvez, M.; Fajardo, V.; Shamma, M. ibid. 1988, C44, 553. (g) Font, J.; Sanchez-Ferrando, F.; Segura, C.; Piniella, J. F.; Jeffrey, G. A.; Ruble, J. R. J. Heterocycl. Chem. 1990, 27, 183. (h) Ammon, H. L.; DeShong, P.; Lessen, T. A. Acta Crystallogr. 1991, C47, 2488. (i) Hynes, R. C. Ibid. 1992, C48, 395. (j) Linden, A. Ibid. 1992, C48, 1514. (k) Parvez, M.; Yu, S.; Keay, B. A. Ibid. 1993, C49, 992.
52. Examples of X-ray structure determination of butenolides: (a) Coggon, P.; Luhan, P. A.; McPhail, A. T. J. Chem. Soc. Perkin Trans. 2 1973, 465. (b) Ružić-Toroš, Ž.; Kojić-Prodić, B. Acta Crystallogr. 1976, B32, 2333. (c) Ružić-Toroš, Ž.; Lazarini, F. Ibid. 1978, B34, 854. (d) Ružić-Toroš, Z.; Leban, I. Ibid. 1978, B34, 1226. (e) Ružić-Toroš, Z.; Kojić-Prodić, B. Ibid. 1982, B38, 1664. (f) Parvez, M.; Fajardo, V.; Shamma, M. ibid. 1988, C44, 553. (g) Font, J.; Sanchez-Ferrando, F.; Segura, C.; Piniella, J. F.; Jeffrey, G. A.; Ruble, J. R. J. Heterocycl. Chem. 1990, 27, 183. (h) Ammon, H. L.; DeShong, P.; Lessen, T. A. Acta Crystallogr. 1991, C47, 2488. (i) Hynes, R. C. Ibid. 1992, C48, 395. (j) Linden, A. Ibid. 1992, C48, 1514. (k) Parvez, M.; Yu, S.; Keay, B. A. Ibid. 1993, C49, 992.
53. Examples of X-ray structure determination of butenolides: (a) Coggon, P.; Luhan, P. A.; McPhail, A. T. J. Chem. Soc. Perkin Trans. 2 1973, 465. (b) Ružić-Toroš, Ž.; Kojić-Prodić, B. Acta Crystallogr. 1976, B32, 2333. (c) Ružić-Toroš, Ž.; Lazarini, F. Ibid. 1978, B34, 854. (d) Ružić-Toroš, Z.; Leban, I. Ibid. 1978, B34, 1226. (e) Ružić-Toroš, Z.; Kojić-Prodić, B. Ibid. 1982, B38, 1664. (f) Parvez, M.; Fajardo, V.; Shamma, M. ibid. 1988, C44, 553. (g) Font, J.; Sanchez-Ferrando, F.; Segura, C.; Piniella, J. F.; Jeffrey, G. A.; Ruble, J. R. J. Heterocycl. Chem. 1990, 27, 183. (h) Ammon, H. L.; DeShong, P.; Lessen, T. A. Acta Crystallogr. 1991, C47, 2488. (i) Hynes, R. C. Ibid. 1992, C48, 395. (j) Linden, A. Ibid. 1992, C48, 1514. (k) Parvez, M.; Yu, S.; Keay, B. A. Ibid. 1993, C49, 992.
54. Examples of X-ray structure determination of butenolides: (a) Coggon, P.; Luhan, P. A.; McPhail, A. T. J. Chem. Soc. Perkin Trans. 2 1973, 465. (b) Ružić-Toroš, Ž.; Kojić-Prodić, B. Acta Crystallogr. 1976, B32, 2333. (c) Ružić-Toroš, Ž.; Lazarini, F. Ibid. 1978, B34, 854. (d) Ružić-Toroš, Z.; Leban, I. Ibid. 1978, B34, 1226. (e) Ružić-Toroš, Z.; Kojić-Prodić, B. Ibid. 1982, B38, 1664. (f) Parvez, M.; Fajardo, V.; Shamma, M. ibid. 1988, C44, 553. (g) Font, J.; Sanchez-Ferrando, F.; Segura, C.; Piniella, J. F.; Jeffrey, G. A.; Ruble, J. R. J. Heterocycl. Chem. 1990, 27, 183. (h) Ammon, H. L.; DeShong, P.; Lessen, T. A. Acta Crystallogr. 1991, C47, 2488. (i) Hynes, R. C. Ibid. 1992, C48, 395. (j) Linden, A. Ibid. 1992, C48, 1514. (k) Parvez, M.; Yu, S.; Keay, B. A. Ibid. 1993, C49, 992.
55. Examples of X-ray structure determination of butenolides: (a) Coggon, P.; Luhan, P. A.; McPhail, A. T. J. Chem. Soc. Perkin Trans. 2 1973, 465. (b) Ružić-Toroš, Ž.; Kojić-Prodić, B. Acta Crystallogr. 1976, B32, 2333. (c) Ružić-Toroš, Ž.; Lazarini, F. Ibid. 1978, B34, 854. (d) Ružić-Toroš, Z.; Leban, I. Ibid. 1978, B34, 1226. (e) Ružić-Toroš, Z.; Kojić-Prodić, B. Ibid. 1982, B38, 1664. (f) Parvez, M.; Fajardo, V.; Shamma, M. ibid. 1988, C44, 553. (g) Font, J.; Sanchez-Ferrando, F.; Segura, C.; Piniella, J. F.; Jeffrey, G. A.; Ruble, J. R. J. Heterocycl. Chem. 1990, 27, 183. (h) Ammon, H. L.; DeShong, P.; Lessen, T. A. Acta Crystallogr. 1991, C47, 2488. (i) Hynes, R. C. Ibid. 1992, C48, 395. (j) Linden, A. Ibid. 1992, C48, 1514. (k) Parvez, M.; Yu, S.; Keay, B. A. Ibid. 1993, C49, 992.
56. Examples of X-ray structure determination of butenolides: (a) Coggon, P.; Luhan, P. A.; McPhail, A. T. J. Chem. Soc. Perkin Trans. 2 1973, 465. (b) Ružić-Toroš, Ž.; Kojić-Prodić, B. Acta Crystallogr. 1976, B32, 2333. (c) Ružić-Toroš, Ž.; Lazarini, F. Ibid. 1978, B34, 854. (d) Ružić-Toroš, Z.; Leban, I. Ibid. 1978, B34, 1226. (e) Ružić-Toroš, Z.; Kojić-Prodić, B. Ibid. 1982, B38, 1664. (f) Parvez, M.; Fajardo, V.; Shamma, M. ibid. 1988, C44, 553. (g) Font, J.; Sanchez-Ferrando, F.; Segura, C.; Piniella, J. F.; Jeffrey, G. A.; Ruble, J. R. J. Heterocycl. Chem. 1990, 27, 183. (h) Ammon, H. L.; DeShong, P.; Lessen, T. A. Acta Crystallogr. 1991, C47, 2488. (i) Hynes, R. C. Ibid. 1992, C48, 395. (j) Linden, A. Ibid. 1992, C48, 1514. (k) Parvez, M.; Yu, S.; Keay, B. A. Ibid. 1993, C49, 992.
57. Gawronski, J. K. In Houben-Weyl Methods of Organic Chemistry, 4th ed., Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1995; Vol. E21a, pp 506-508.
58. It is apparent that of the two allylic bonds at C(5), C-alkyl (or C-alkoxy), and CH, each having opposite helicity relation to the C=C bond, the former, more polarizable, has a dominating effect on the sign of the π-π* Cotton effect; see earlier work on allylic axial chirality effect: (a) Beecham, A. F.; Mathieson, A. McL.; Johns, S. R.; Lamberton, J. A.; Sioumis, A. A., Batterham, T. J.; Young, I. G. Tetrahedron 1971, 27, 3726. (b) Beecham, A. F. Ibid. 1971, 27, 5207. (c) Scott, A. I.; Wrixon, A. D. Ibid. 1971, 27, 4787. (d) Totty, R. N.; Hudec, J. J. Chem. Soc., Chem. Commun. 1971, 785. (e) Burgstahler, A. W.; Barkhurst, R C.; Gawronski, J. K. In Modern Methods of Steroid Analysis; Heftmann, E., Ed.; Academic Press: New York, 1973; pp 349-379.
59. It is apparent that of the two allylic bonds at C(5), C-alkyl (or C-alkoxy), and CH, each having opposite helicity relation to the C=C bond, the former, more polarizable, has a dominating effect on the sign of the π-π* Cotton effect; see earlier work on allylic axial chirality effect: (a) Beecham, A. F.; Mathieson, A. McL.; Johns, S. R.; Lamberton, J. A.; Sioumis, A. A., Batterham, T. J.; Young, I. G. Tetrahedron 1971, 27, 3726. (b) Beecham, A. F. Ibid. 1971, 27, 5207. (c) Scott, A. I.; Wrixon, A. D. Ibid. 1971, 27, 4787. (d) Totty, R. N.; Hudec, J. J. Chem. Soc., Chem. Commun. 1971, 785. (e) Burgstahler, A. W.; Barkhurst, R C.; Gawronski, J. K. In Modern Methods of Steroid Analysis; Heftmann, E., Ed.; Academic Press: New York, 1973; pp 349-379.
60. It is apparent that of the two allylic bonds at C(5), C-alkyl (or C-alkoxy), and CH, each having opposite helicity relation to the C=C bond, the former, more polarizable, has a dominating effect on the sign of the π-π* Cotton effect; see earlier work on allylic axial chirality effect: (a) Beecham, A. F.; Mathieson, A. McL.; Johns, S. R.; Lamberton, J. A.; Sioumis, A. A., Batterham, T. J.; Young, I. G. Tetrahedron 1971, 27, 3726. (b) Beecham, A. F. Ibid. 1971, 27, 5207. (c) Scott, A. I.; Wrixon, A. D. Ibid. 1971, 27, 4787. (d) Totty, R. N.; Hudec, J. J. Chem. Soc., Chem. Commun. 1971, 785. (e) Burgstahler, A. W.; Barkhurst, R C.; Gawronski, J. K. In Modern Methods of Steroid Analysis; Heftmann, E., Ed.; Academic Press: New York, 1973; pp 349-379.
61. It is apparent that of the two allylic bonds at C(5), C-alkyl (or C-alkoxy), and CH, each having opposite helicity relation to the C=C bond, the former, more polarizable, has a dominating effect on the sign of the π-π* Cotton effect; see earlier work on allylic axial chirality effect: (a) Beecham, A. F.; Mathieson, A. McL.; Johns, S. R.; Lamberton, J. A.; Sioumis, A. A., Batterham, T. J.; Young, I. G. Tetrahedron 1971, 27, 3726. (b) Beecham, A. F. Ibid. 1971, 27, 5207. (c) Scott, A. I.; Wrixon, A. D. Ibid. 1971, 27, 4787. (d) Totty, R. N.; Hudec, J. J. Chem. Soc., Chem. Commun. 1971, 785. (e) Burgstahler, A. W.; Barkhurst, R C.; Gawronski, J. K. In Modern Methods of Steroid Analysis; Heftmann, E., Ed.; Academic Press: New York, 1973; pp 349-379.
62. It is apparent that of the two allylic bonds at C(5), C-alkyl (or C-alkoxy), and CH, each having opposite helicity relation to the C=C bond, the former, more polarizable, has a dominating effect on the sign of the π-π* Cotton effect; see earlier work on allylic axial chirality effect: (a) Beecham, A. F.; Mathieson, A. McL.; Johns, S. R.; Lamberton, J. A.; Sioumis, A. A., Batterham, T. J.; Young, I. G. Tetrahedron 1971, 27, 3726. (b) Beecham, A. F. Ibid. 1971, 27, 5207. (c) Scott, A. I.; Wrixon, A. D. Ibid. 1971, 27, 4787. (d) Totty, R. N.; Hudec, J. J. Chem. Soc., Chem. Commun. 1971, 785. (e) Burgstahler, A. W.; Barkhurst, R C.; Gawronski, J. K. In Modern Methods of Steroid Analysis; Heftmann, E., Ed.; Academic Press: New York, 1973; pp 349-379.
63. See, for example: Hoye, T. R.; Humpal, P. E.; Jiménez, J. I.; Mayer, M. J.; Tan, L., Ye, Z. Tetrahedron Lett. 1994, 35, 7517.
64. Gawronski, J. K.; Wu, Y.-C. Unpublished results.
65. Published CD data on acetogenins. Reticulatacin: Saad, J. M.; Hui, Y.-H.; Rupprecht, J. K.; Anderson, J. E.; Kozlowski, J. F.; Zhao, G.; Wood, K. V.; McLaughlin, J. L. Tetrahedron 1991, 47, 2751. Bullatalicin: Hui, Y.-H.; Rupprecht, J. K.; Anderson, J. E.; Liv, Y.-M.; Smith, D. L.; Chang, Ch.-J.; McLaughlin, J. L. Tetrahedron 1989, 45, 6941. Bullatacin, asimicin, rolliniastatin: Hui, Y -H.; Rupprecht, J. K.; Liu, Y.-M.; Anderson, J. E.; Smith, D. L.; Chang, C.-J.; McLaughlin, J. L. J. Nat. Prod. 1989, 52, 463. On the basis of the CD data the absolute configuration at C(36) of buliatacin as shown in this paper should be reversed.
66. Published CD data on acetogenins. Reticulatacin: Saad, J. M.; Hui, Y.-H.; Rupprecht, J. K.; Anderson, J. E.; Kozlowski, J. F.; Zhao, G.; Wood, K. V.; McLaughlin, J. L. Tetrahedron 1991, 47, 2751. Bullatalicin: Hui, Y.-H.; Rupprecht, J. K.; Anderson, J. E.; Liv, Y.-M.; Smith, D. L.; Chang, Ch.-J.; McLaughlin, J. L. Tetrahedron 1989, 45, 6941. Bullatacin, asimicin, rolliniastatin: Hui, Y -H.; Rupprecht, J. K.; Liu, Y.-M.; Anderson, J. E.; Smith, D. L.; Chang, C.-J.; McLaughlin, J. L. J. Nat. Prod. 1989, 52, 463. On the basis of the CD data the absolute configuration at C(36) of buliatacin as shown in this paper should be reversed.
67. Published CD data on acetogenins. Reticulatacin: Saad, J. M.; Hui, Y.-H.; Rupprecht, J. K.; Anderson, J. E.; Kozlowski, J. F.; Zhao, G.; Wood, K. V.; McLaughlin, J. L. Tetrahedron 1991, 47, 2751. Bullatalicin: Hui, Y.-H.; Rupprecht, J. K.; Anderson, J. E.; Liv, Y.-M.; Smith, D. L.; Chang, Ch.-J.; McLaughlin, J. L. Tetrahedron 1989, 45, 6941. Bullatacin, asimicin, rolliniastatin: Hui, Y -H.; Rupprecht, J. K.; Liu, Y.-M.; Anderson, J. E.; Smith, D. L.; Chang, C.-J.; McLaughlin, J. L. J. Nat. Prod. 1989, 52, 463. On the basis of the CD data the absolute configuration at C(36) of buliatacin as shown in this paper should be reversed.
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