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Journal of Organic Chemistry

Volumn 73, Issue 15, 2008, Pages 5723-5731

Calculated chemical shifts as a fine tool of conformational analysis: An unambiguous solution for haouamine alkaloids

(1) Belostotskii, Anatoly M a

a BAR ILAN UNIVERSITY (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; ARSENIC COMPOUNDS; CHEMICAL REACTIONS; CHEMICAL SHIFT; FOOD PROCESSING; MODEL STRUCTURES; MOLECULAR MECHANICS; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REGRESSION ANALYSIS; SPEED;

AB INITIO CALCULATIONS; ACETONE SOLUTIONS; B3LYP/6 31G; CARBON ATOMS; CHEMICAL EQUATIONS; CONFORMATIONAL ANALYSIS (CA); CONFORMATIONAL SPACES; CONFORMATIONAL STUDIES; ENERGY CONFORMERS; IMPLICIT MODELLING; INTERCONVERSION; LOW-ENERGY STRUCTURES; MOLECULAR MECHANICS CALCULATIONS; PARACYCLOPHANE; REGRESSION (R2); RELATIVE ENERGIES; SOLVATION SHELLS;

CHEMICAL ANALYSIS;

ACETONE; ALKALOID DERIVATIVE; CARBON; HAOUAMINE A; PARACYCLOPHANE DERIVATIVE; POLYFUNCTIONAL GROUP;

AB INITIO CALCULATION; ACCURACY; ARTICLE; CALCULATED CHEMICAL SHIFT; CALCULATION; CHEMICAL STRUCTURE; CONFORMATION; DENSITY FUNCTIONAL THEORY; ENERGY; GEOMETRY; MOLECULAR MECHANICS; PROTON NUCLEAR MAGNETIC RESONANCE; REGRESSION ANALYSIS; ROTATION; SOLVATION; VALIDATION PROCESS;

EID: 48249147835 PISSN: 00223263 EISSN: None Source Type: Journal
DOI: 10.1021/jo702766x Document Type: Article

Times cited : (31)

References (59)

1
- 0037462329
- Garrido, L.; Zubía, E.; Ortega, M. J.; Salvá, J. J. Org. Chem. 2003, 68, 293-299.
- (2003) J. Org. Chem , vol.68 , pp. 293-299
- Garrido, L.¹ Zubía, E.² Ortega, M.J.³ Salvá, J.⁴

2
- 0345707540
- Kaucher, M. S.; Jarvis, B. B. Chemtracts Org. Chem. 2003, 16, 692-694.
- (2003) Chemtracts Org. Chem , vol.16 , pp. 692-694
- Kaucher, M.S.¹ Jarvis, B.B.²

3
- 48249116649
- In the original text: .isomer I could have a stereochemistry as represented in Figure. This accurate NMR study1 reasonably doesn't claim that the obtained ROESY correlations indicate a sole geometry of the tetrahydropyridine ring of M1 in solution. Indeed, these experimental NOE-based data are compatible with a 1Sf and Sf1 sofa as well as a 1H6 half-chair conformation see Supporting Information
- 6 half-chair conformation (see Supporting Information).

4
- 48249116259
- Concerning rotation, it is discussed1 as atropoisomerism of the 3-aza-[7]-paracyclophane system. This description of rotation may be interpreted only as rotation of ring B. Geometries, which result from the proposed rotation or N-inversion in C1, are not specified in ref 1. The only source of structures C3 or C2/C4 are the present calculations. On the other hand, formally, these structures may be obtained via rotation of ring B or N-inversion. respectively (Figure 2; see Figure 3 for similar structures, No other conformers, which could appear as a result of these intramolecular motions, e.g, additional ring B rotamers, have been located (this work, Thus, conformers C2, C3, C4, etc. correspond to general structures implied in ref 1. In fact, rotation of ring B is clerically hindered see Supporting Information for details, However, consideration of interconversions C1, C3, C5, C7, etc. cannot be withdrawn. For instance, add
- f in Figures 2 and 3 means formal rotation of phenolic ring B.

5
- 0003727896
- Rabideau, P. W, Ed, VCH Publishers: New-York
- (a) Anet, F. A. L. In Conformational Analysis of Cyclohexenes, Cyclohexadienes and Related Hydroaromatic Compounds; Rabideau, P. W., Ed.; VCH Publishers: New-York, 1989; pp 3-45.
- (1989) Conformational Analysis of Cyclohexenes, Cyclohexadienes and Related Hydroaromatic Compounds , pp. 3-45
- Anet, F.A.L.¹

6
- 0037184765
- (b) Belostotskii, A. M.; Gottlieb, H. E.; Shokhen, M. J. Org. Chem. 2002, 67, 9257-9266.
- (2002) J. Org. Chem , vol.67 , pp. 9257-9266
- Belostotskii, A.M.¹ Gottlieb, H.E.² Shokhen, M.³

7
- 5844223038
- Lambert, J. B, Takeuchi, E, Eds, VCH Publishers: New York
- (a) Jennings, W. B.; Boyd, D. R. In Cyclic Organonitrogen Stereodynamics; Lambert, J. B., ; Takeuchi, E., Eds.; VCH Publishers: New York, 1992; pp 107-158.
- (1992) Cyclic Organonitrogen Stereodynamics , pp. 107-158
- Jennings, W.B.¹ Boyd, D.R.²

8
- 0000854993
- (b) Nelsen, S. F.; Ippoliti, J. T.; Frigo, T. B. ; Petillo, P. A. J. Am. Chem. Soc. 1989, 111, 1776-1781.
- (1989) J. Am. Chem. Soc , vol.111 , pp. 1776-1781
- Nelsen, S.F.¹ Ippoliti, J.T.² Frigo, T.B.³ Petillo, P.A.⁴

9
- 0001620328
- (c) Belostotskii, A. M.; Hassner. A. J. Phys. Org. Chem. 1999, 12, 659-663.
- (1999) J. Phys. Org. Chem , vol.12 , pp. 659-663
- Belostotskii, A.M.¹ Hassner, A.²

10
- 0037453637
- (d) Belostotskii, A. M.; Markevich, E. J. Org. Chem. 2003, 68, 3055-3063.
- (2003) J. Org. Chem , vol.68 , pp. 3055-3063
- Belostotskii, A.M.¹ Markevich, E.²

11
- 0035900961
- (a) Yamada, H.; Yonehara, S.; Tanaka, S.; Muro, F.; Watanabe, A.; Nishikawa, K. J. Am. Chem. Soc. 2001, 123, 279-284.
- (2001) J. Am. Chem. Soc , vol.123 , pp. 279-284
- Yamada, H.¹ Yonehara, S.² Tanaka, S.³ Muro, F.⁴ Watanabe, A.⁵ Nishikawa, K.⁶

12
- 0012020113
- (b) Whitesides, G. M.; Pawson, B. A.; Cope, A. C. J. Amer. Chem. Soc. 1968, 90, 639-644.
- (1968) J. Amer. Chem. Soc , vol.90 , pp. 639-644
- Whitesides, G.M.¹ Pawson, B.A.² Cope, A.C.³

13
- 0035149501
- (c) Scharwächter, K. P.; Hochmuth, D. H.; Dittmann, H.; König, W. A. Chirality 2001, 13, 679-690.
- (2001) Chirality , vol.13 , pp. 679-690
- Scharwächter, K.P.¹ Hochmuth, D.H.² Dittmann, H.³ König, W.A.⁴

14
- 0000338260
- (a) Bushweller, C. H.; Anderson, W. G.; Stevenson, P. E.; Burkey, D. L.; O'Neil, J. W. J. Am. Chem. Soc. 1974, 96, 3892-3900.
- (1974) J. Am. Chem. Soc , vol.96 , pp. 3892-3900
- Bushweller, C.H.¹ Anderson, W.G.² Stevenson, P.E.³ Burkey, D.L.⁴ O'Neil, J.W.⁵

15
- 0000020144
- (b) Belostotskii, A. M.; Aped, P.; Hassner, A. J. Mol. Struct. (THEOCHEM) 1997, 398-399, 427-434.
- (1997) J. Mol. Struct. (THEOCHEM) , vol.398-399 , pp. 427-434
- Belostotskii, A.M.¹ Aped, P.² Hassner, A.³

16
- 0001495620
- (a) Malarski, Z.; Rospenk, L.; Sobczyk, L.; Grech, E. J. Chem. Phys. 1982, 86, 401-406.
- (1982) J. Chem. Phys , vol.86 , pp. 401-406
- Malarski, Z.¹ Rospenk, L.² Sobczyk, L.³ Grech, E.⁴

17
- 0031559456
- Majerz, 1.; Malarski, Z.; Sobczyk, L. Chem. Phys. Lett. 1997, 274, 361-364.
- (b) Majerz, 1.; Malarski, Z.; Sobczyk, L. Chem. Phys. Lett. 1997, 274, 361-364.

18
- 48249091122
- Ratajczak, H. Electron Proton Transfer Chem. Biol. 1992, 78, 293-310.
- (c) Ratajczak, H. Electron Proton Transfer Chem. Biol. 1992, 78, 293-310.

19
- 37049079512
- (d) Ilchzyszyn, M.; Ratajczak, H. J. Chem. Soc., Faraday Trans. 1995, 91, 3859-3867.
- (1995) J. Chem. Soc., Faraday Trans , vol.91 , pp. 3859-3867
- Ilchzyszyn, M.¹ Ratajczak, H.²

20
- 84989078589
- (c) Denisov, G. S.; Gindin, V. A.; Golubev, N. S.; Koltsov, A. I.; Smirnov, S. N.; Rospenk, M.; Koll, A.; Sobczyk, L. Magn. Reson. Chem. 1993, 31, 1034-1037.
- (1993) Magn. Reson. Chem , vol.31 , pp. 1034-1037
- Denisov, G.S.¹ Gindin, V.A.² Golubev, N.S.³ Koltsov, A.I.⁴ Smirnov, S.N.⁵ Rospenk, M.⁶ Koll, A.⁷ Sobczyk, L.⁸

21
- 0027882503
- (a) Bühl, M.; Gauss, J.; Hofmann, M.; Scheleyer, P. v. R. J. Am. Chem. Soc. 1993, 115, 12385.
- (1993) J. Am. Chem. Soc , vol.115 , pp. 12385
- Bühl, M.¹ Gauss, J.² Hofmann, M.³ Scheleyer, P.V.R.⁴

22
- 0000304948
- (b) Tannor, D. J.; Marten, B.; Murphy, R. P.; Friesner, R. A.; Sitkoff, D.; Nicolls, A.; Ringhalda, M.; Goddard, W. A.; Honig, B. J. Am. Chem. Soc. 1994, 116, 11875.
- (1994) J. Am. Chem. Soc , vol.116 , pp. 11875
- Tannor, D.J.¹ Marten, B.² Murphy, R.P.³ Friesner, R.A.⁴ Sitkoff, D.⁵ Nicolls, A.⁶ Ringhalda, M.⁷ Goddard, W.A.⁸ Honig, B.⁹

23
- 40749094858
- (c) Ditchfield, R. Mol. Phys. 1974, 27, 789-807.
- (1974) Mol. Phys , vol.27 , pp. 789-807
- Ditchfield, R.¹

24
- 9444290281
- (d) Gauss, J. J. Chem. Phys. 1993, 99, 3629-3643.
- (1993) J. Chem. Phys , vol.99 , pp. 3629-3643
- Gauss, J.¹

25
- 11744305193
- (e) Wolinski, K.; Hinton, J. F.; Pulay, P. J. Am. Chem. Soc. 1990, 112, 8251-8260.
- (1990) J. Am. Chem. Soc , vol.112 , pp. 8251-8260
- Wolinski, K.¹ Hinton, J.F.² Pulay, P.³

26
- 40749094858
- (a) Ditchfield, R. Mol. Phys. 1974, 27, 789-807.
- (1974) Mol. Phys , vol.27 , pp. 789-807
- Ditchfield, R.¹

27
- 9444290281
- (b) Gauss, J. J. Chem. Phys. 1993, 99, 3629-3643.
- (1993) J. Chem. Phys , vol.99 , pp. 3629-3643
- Gauss, J.¹

28
- 11744305193
- (c) Wolinski, K.; Hinton, J. F.; Pulay, P. J. Am. Chem. Soc. 1990, 112, 8251-8260.
- (1990) J. Am. Chem. Soc , vol.112 , pp. 8251-8260
- Wolinski, K.¹ Hinton, J.F.² Pulay, P.³

29
- 1242268874
- (a) Cheeseman, J. R.; Trucks, G. W.; Keith, T. A.; Frisch, M. J. J. Chem. Phys. 1996, 104, 5497-5509.
- (1996) J. Chem. Phys , vol.104 , pp. 5497-5509
- Cheeseman, J.R.¹ Trucks, G.W.² Keith, T.A.³ Frisch, M.J.⁴

30
- 9644307594
- (b) Facelli, J. C. Concepts Magn. Reson. 2004, 20A, 42-69.
- (2004) Concepts Magn. Reson , vol.20 A , pp. 42-69
- Facelli, J.C.¹

31
- 2142649243
- (c) Jimeno, M. L.; Alkorta, I.; Elguero, J.; Anderson, J. E.; Claramunt, R. M.; Lavandera, J. L. New J. Chem. 1998, 1079-1083.
- (1998) New J. Chem , pp. 1079-1083
- Jimeno, M.L.¹ Alkorta, I.² Elguero, J.³ Anderson, J.E.⁴ Claramunt, R.M.⁵ Lavandera, J.L.⁶

32
- 0000599309
- (d) Alkorta, I.; Elguero, J. New J. Chem. 1998, 381-385.
- (1998) New J. Chem , pp. 381-385
- Alkorta, I.¹ Elguero, J.²

33
- 0030813732
- (e) Forsyth, D. A.; Sebag, A. B. J. Am. Chem. Soc. 1997, 119, 9483-9494.
- (1997) J. Am. Chem. Soc , vol.119 , pp. 9483-9494
- Forsyth, D.A.¹ Sebag, A.B.²

34
- 33644951349
- (f) Lobato-García, C. E.; Guadarrama, P.; Lozada, C.; Enríquez, R. G.; Gnecco, D.; Reynolds, W. F. J. Mol. Struct. 2006, 786, 53-64.
- (2006) J. Mol. Struct , vol.786 , pp. 53-64
- Lobato-García, C.E.¹ Guadarrama, P.² Lozada, C.³ Enríquez, R.G.⁴ Gnecco, D.⁵ Reynolds, W.F.⁶

35
- 48249083675
- (g) Costa, V. E. U.; Grunewald-Nichele, A.; Carneiro, J. W. M. J. Mol. Struct. 2004, 702, 71-76.
- (2004) J. Mol. Struct , vol.702 , pp. 71-76
- Costa, V.E.U.¹ Grunewald-Nichele, A.² Carneiro, J.W.M.³

36
- 0036675524
- (h) Wang, B.; Miskolizie, M.; Kotovych, G.; Pulay, P. J. Biomol. Struct. Dyn. 2002, 20, 71-80.
- (2002) J. Biomol. Struct. Dyn , vol.20 , pp. 71-80
- Wang, B.¹ Miskolizie, M.² Kotovych, G.³ Pulay, P.⁴

37
- 34047251978
- (i) Přecechtělová, J.; Munzarová, M. L.; Novák, P.; Sklenář, V. J. Phys. Chem. B 2007, 111, 2658-2667.
- (2007) J. Phys. Chem. B , vol.111 , pp. 2658-2667
- Přecechtělová, J.¹ Munzarová, M.L.² Novák, P.³ Sklenář, V.⁴

38
- 10944237213
- (j) Migda, W.; Rys, B. Magn. Reson. Chem. 2004, 459-466.
- (2004) Magn. Reson. Chem , pp. 459-466
- Migda, W.¹ Rys, B.²

39
- 29944432123
- (k) Gill, G.; Pawar, D. M.; Noe, E. A. J. Org. Chem. 2005, 70, 10726-10731.
- (2005) J. Org. Chem , vol.70 , pp. 10726-10731
- Gill, G.¹ Pawar, D.M.² Noe, E.A.³

40
- 0039005978
- (l) Vrček, V.; Kronja, O.; Siehl, H.-U. J. Chem. Soc., Perkin Trans. 2 1999, 1317-1321.
- (1999) J. Chem. Soc., Perkin Trans. 2 , pp. 1317-1321
- Vrček, V.¹ Kronja, O.² Siehl, H.-U.³

41
- 0035977237
- Sebag, A. B.; Forsyth, D. A.; Plante, M. A. J. Org. Chem. 2001, 66, 7967-7973.
- (2001) J. Org. Chem , vol.66 , pp. 7967-7973
- Sebag, A.B.¹ Forsyth, D.A.² Plante, M.A.³

42
- 10044259589
- Belostotskii, A. M.; Goren, Z.; Gottlieb, H. E. J. Nat. Prod. 2004, 67, 1842-1849.
- (2004) J. Nat. Prod , vol.67 , pp. 1842-1849
- Belostotskii, A.M.¹ Goren, Z.² Gottlieb, H.E.³

43
- 84961983851
- (a) Nagy, P.; Alagona, G.; Ghio, C.; Takacs-Novak, K. J. Am. Chem. Soc. 2003, 125, 2770-2785.
- (2003) J. Am. Chem. Soc , vol.125 , pp. 2770-2785
- Nagy, P.¹ Alagona, G.² Ghio, C.³ Takacs-Novak, K.⁴

44
- 0037608031
- (b) Schäfer, T.; Beaulieu, C.; Sebastian, R. Can. J. Chem. 1991, 69, 503-508.
- (1991) Can. J. Chem , vol.69 , pp. 503-508
- Schäfer, T.¹ Beaulieu, C.² Sebastian, R.³

45
- 0006108394
- (c) Schäfer, T.; Kunkel, J. P.; Shurko, R. W.; Bernard, G. M. Can. J. Chem. 1994, 72, 1722-1777.
- (1994) Can. J. Chem , vol.72 , pp. 1722-1777
- Schäfer, T.¹ Kunkel, J.P.² Shurko, R.W.³ Bernard, G.M.⁴

46
- 0043109623
- (a) Belhekar, A. A.; Agashe, M. S.; Jose, C. I. J. Chem. Soc., Faraday Trans. 1990, 86, 1781-1784.
- (1990) J. Chem. Soc., Faraday Trans , vol.86 , pp. 1781-1784
- Belhekar, A.A.¹ Agashe, M.S.² Jose, C.I.³

47
- 2742574832
- (b) Bock, C. W.; Trachtman, M. THEOCHEM 1986, 32, 63-74.
- (1986) THEOCHEM , vol.32 , pp. 63-74
- Bock, C.W.¹ Trachtman, M.²

48
- 0037016451
- Int. Ed
- Steiner, T. Angw. Chem., Int. Ed. 2002, 41, 48-76.
- (2002) Angw. Chem , vol.41 , pp. 48-76
- Steiner, T.¹

49
- 48249105361
- Bushweller, C. H. In Acyclic Organonitrogen Stereodynamics; Lambert, J. B, ; Takeuchi, E., Eds.; VCH Publishers: New York, 1992; pp 1-55.
- (a) Bushweller, C. H. In Acyclic Organonitrogen Stereodynamics; Lambert, J. B, ; Takeuchi, E., Eds.; VCH Publishers: New York, 1992; pp 1-55.

50
- 48249118210
- (b) Belostotskii, A. M. Trends Heterocycl. Chem. 2005, 10, 23-45.
- (2005) Trends Heterocycl. Chem , vol.10 , pp. 23-45
- Belostotskii, A.M.¹

51
- 0001570631
- (a) Anderson, J. E.; Tocher, D. A.; Corrie, J. E. T.; Lunazzi, L. J. Am. Chem. Soc. 1993, 115, 3494-3499.
- (1993) J. Am. Chem. Soc , vol.115 , pp. 3494-3499
- Anderson, J.E.¹ Tocher, D.A.² Corrie, J.E.T.³ Lunazzi, L.⁴

52
- 0032971681
- (b) Belostotskii, A. M.; Gottlieb, H. E.; Aped, P.; Hassner, A. Chem. Eur. J. 1999, 5, 449-455.
- (1999) Chem. Eur. J , vol.5 , pp. 449-455
- Belostotskii, A.M.¹ Gottlieb, H.E.² Aped, P.³ Hassner, A.⁴

53
- 0037007897
- (c) Belostotskii, A. M.; Gottlieb, H. E.; Aped, P. Chem. Eur. J. 2002, 8, 3016-3026.
- (2002) Chem. Eur. J , vol.8 , pp. 3016-3026
- Belostotskii, A.M.¹ Gottlieb, H.E.² Aped, P.³

54
- 48249083310
- The opposite is incorrect: NIR and some rotations may be not coupled with RI (see Section 3a).
- The opposite is incorrect: NIR and some rotations may be not coupled with RI (see Section 3a).

55
- 0007793280
- (a) Saunders, M.; Houk, K. N.; Wu, Y. D.; Still, W. C.; Lipton, M.; Chang, G.; Guida, W. C. J. Am. Chem. Soc. 1990, 112, 1419-1427.
- (1990) J. Am. Chem. Soc , vol.112 , pp. 1419-1427
- Saunders, M.¹ Houk, K.N.² Wu, Y.D.³ Still, W.C.⁴ Lipton, M.⁵ Chang, G.⁶ Guida, W.C.⁷

56
- 84986437005
- (b) Mohamadi, F.; Richards, N. G.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem, 1990, 11, 440-467.
- (1990) J. Comput. Chem , vol.11 , pp. 440-467
- Mohamadi, F.¹ Richards, N.G.² Guida, W.C.³ Liskamp, R.⁴ Lipton, M.⁵ Caufield, C.⁶ Chang, G.⁷ Hendrickson, T.⁸ Still, W.C.⁹

57
- 48249091543
- Macromodel, Version 6.5; Department of Chemistry, Columbia University: New York
- (c) Macromodel, Version 6.5; Department of Chemistry, Columbia University: New York.

58
- 0003934843
- Schrödinger, Inc, Portland, OR
- Jaguar 4.0; Schrödinger, Inc.: Portland, OR, 1991-2000.
- (1991) Jaguar 4.0

59
- 0004133516
- Gaussian, Inc, Pittsburgh PA
- Gaussian98; Gaussian, Inc.: Pittsburgh PA, 1998.
- (1998) Gaussian98

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