Optical rotation computation, total synthesis, and stereochemistry assignment of the marine natural product pitiamide A

Journal of the American Chemical Society

Volumn 122, Issue 19, 2000, Pages 4608-4617

  Ribe, Seth ^a   Kondru, Rama K ^a   Beratan, David N ^a   Wipf, Peter ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LIPID; NATURAL PRODUCT; PITIAMIDE A; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034678996     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9945313     Document Type: Article

References (101)

1. Nagle, D. G.; Park, P. U.; Paul, V. J. Tetrahedron Lett. 1997, 38, 6969.
2. Possibly because of instabilities in the polarimeter, the actual measurements fluctuated from -15.3 to -8.7. Prof. V. Paul, personal communication.
3. Kondru, R. K.; Wipf, P.; Beratan, D. N. J. Am. Chem. Soc. 1998, 120, 2204.
4. Kondru, R. K.; Wipf, P.; Beratan, D. N. J. Phys. Chem. 1999, 103, 6603.
5. (a) van't Hoff, J. H. Arch. Neerl. Sci. Exactes Nat. 1874, 9, 455.
6. (b) van't Hoff, J. H. Die Lagerung der Atome im Raume; Vieweg: Braunschweig, Germany, 1894; p 95.
7. Kondru, R. K.; Lim, S.; Wipf, P.; Beratan, D. N. Chirality 1997, 9, 469.
8. Wipf, P.; Lim, S. Chimia 1996, 50, 157.
9. See also: McDonald, D. Q.; Still, W. C. Tetrahedron Lett. 1992, 33, 7747.
10. Van Gunsteren, W. F.; Berendsen, H. J. C. Mol. Simul. 1988, 1, 173.
11. Still, W. C.; Tempczyk, A.; Hawley, R. C.; Hendrickson, T. J. Am. Chem. Soc. 1990, 112, 6127.
12. Calculations of the optical rotation of hydrogen-bonded conformations of C(5)-C(14) segments of pitiamide A provided absolute values that were in the same order of magnitude as open-chain conformations. These control studies addressed the potential pitfall that small percentages of intramolecular hydrogen-bonded conformations could significantly alter the overall optical rotation of pitiamide A and thus introduce a major source of error in our computational strategy.
13. Kondru, R. K.; Chen, C. H.-T.; Curran, D. P.; Beratan, D. N.; Wipf, P. Tetrahedron: Asymmetry 1999, 10, 4143.
14. Walden, P. Z. Phys. Chem. 1894, 15, 196.
15. Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; Wiley: New York, 1994.
16. Nakanishi, K.; Berova, N.; Woody, R. W. Circular Dichroism Principles and Applications; VCH Publishers Inc.: New York, 1994.
17. Kauzmann, W.; Eyring, H. J. Chem. Phys. 1941, 9, 41.
18. Freudenberg, K.; Todd, J.; Seidler, R. Ann. Chem. 1933, 501, 199.
19. Brewster, J. H. J. Am. Chem. Soc. 1959, 81, 5475.
20. Brewster, J. H. Tetrahedron 1961, 13, 106.
21. Moscowitz, A. Adv. Chem. Phys. 1962, 4, 67.
22. Applequist, J. J. Chem. Phys. 1973, 58, 4251.
23. Tinoco, I., Jr.; Woody, R. W. J. Chem. Phys. 1964, 40, 160.
24. Sathyanarayana, B. K.; Stevens, E. S. J. Org. Chem. 1987, 52, 3170.
25. Gould, R. R.; Hoffmann, R. J. Am. Chem. Soc. 1970, 92, 1813.
26. Pao, Y. H.; Santry, D. P. J. Am. Chem. Soc. 1966, 88, 4157.
27. Kuhn, W. Stereochemie; Freudenberg, K., Ed.; Deuticke: Leipzig, 1933; Chapter 8, p 394.
28. Born, M. Proc. R. Soc. London A 1935, 150, 84.
29. Kirkwood, J. G. J. Chem. Phys. 1937, 5, 479.
30. Nolte, H. J.; Buss, V. Tetrahedron 1975, 31, 719.
31. Maestro, M.; Moccia, R.; Taddei, G. Theor. Chim. Acta 1967, 8, 80.
32. Eyring, H.; Walter, J.; Kimball, G. E. Quantum Chemistry; Wiley: New York, 1944.
33. Rauk, A.; Barriel, J. M. Chem. Phys. 1977, 25, 409.
34. Bak, K. L.; Hansen, A. E.; Ruud, K.; Helgaker, T.; Olsen, J.; Jørgensen, P. Theor. Chim. Acta. 1995, 90, 441.
35. Hansen, A. E.; Bouman, T. D. J. Am. Chem. Soc. 1985, 107, 4828.
36. Snatzke, G. In Chirality: from Weak Bosons to the Alpha-Helix; Janoschek, R., Ed.; Springer-Verlag: Berlin, 1991; pp 59-85.
37. Costante, J.; Hecht, L.; Polavarapu, P. L.; Collet, A.; Barron, L. D. Angew. Chem., Int. Ed. Engl. 1997, 36, 885.
38. Polavarapu, P. L. Mol. Phys. 1997, 91, 551.
39. Kondru, R. K.; Wipf, P.; Beratan, D. N. Science 1998, 282, 2247.
40. Polavarapu, P. L. Tetrahedron: Asymmetry 1997, 8, 3397.
41. (a) Polavarapu, P. L.; Chakraborty, D. K. J. Am. Chem. Soc. 1998, 120, 6160.
42. (b) Polavarapu, P. L.; Zhao, C. J. Am. Chem. Soc. 1999, 121, 246.
43. Rosenfeld, L. Z. Physik 1928, 52, 161.
44. Amos, R. D. Chem. Phys. Lett. 1982, 87, 23.
45. Amos, R. D.; Rice, J. E. The Cambridge Analytic Derivative Package; issue 6.3, Cambridge, U.K., 1997.
46. Helgaker, T.; Jensen, H. J. A.; Olsen, J.; Ruud, K.; Anderson, A. T.; Bak, K. L.; Bakken, V.; Christiansen, O.; Dahle, P.; Dalskov, E. K.; Enevoldsen, T.; Fernandez, B.; Heiberg, H.; Hettema, H.; Jonsson, D.; Kirpekar, S.; Kobayashi, R.; Koch, H.; Mikkelsen, K. V.; Norman, P.; Packer, P.; Saue, T.; Taylor, P. R.; Vahtras, O.; DALTON, an electronic structure program, Release 1.0, 1997.
47. (a) Kauzmann, W.; Eyring, H. J. Chem. Phys. 1941, 9, 41.
48. (b) Arndt, E. R.; Stevens, E. S. Biopolym. 1994, 34, 1527.
49. (c) Arndt, E. R.; Stevens, E. S. Biopolymers 1996, 38, 567.
50. (d) Johnson, W. C.; Tinoco, I. J. Am. Chem. Soc. 1972, 94, 4389.
51. (e) Schellman, J. A. J. Chem. Phys. 1966, 44, 55.
52. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440.
53. Pettersson, I.; Liljefors, T. In Reviews in Conputational Chemistry; Lipkowitz, K. B., Boyd, D. B., Eds.; VCH: New York, 1996; Vol. 9, p 167.
54. Calculations were performed on a 600 MHz dec-alpha workstation and required between 4 and 12 days of CPU time for each fragment.
55. Mynderse, J. S.; Moore, R. E. Phytochem. 1978, 17, 1325.
56. (a) Hughes, D. L. Org. Prep. Proc. Int. 1996, 28, 127.
57. (b) Hughes, D. L. Org. React. 1992, 42, 335.
58. (c) Mitsunobu, O. Synthesis 1981, 1.
59. Fukuyama, T.; Jow, C.-K.; Cheung, M. Tetrahedron Lett. 1995, 36, 6373.
60. For N-methylation of a nosylated amide, see: Katagiri, N.; Takebayashi, M.; Kokufuda, H.; Kaneko, C.; Kanehira, K.; Torihara, M. J. Org. Chem. 1997, 62, 1580.
61. Evans, D. A.; Ennis, M. D.; Mathre, D. J. J. Am. Chem. Soc. 1982, 104, 1737.
62. (a) Kondakov, D. Y.; Negishi, E.-I. J. Am. Chem. Soc. 1995, 117, 10771.
63. (b) Kondakov, D. Y.; Negishi, E.-I. J. Am. Chem. Soc. 1996, 118, 1577.
64. (a) Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 827-874.
65. (b) Johnson, W. S.; Werthemann, L.; Bartlett, W. R.; Brocksom, T. J.; Li, T.-T.; Faulkner, D. J.; Petersen, M. R. J. Am. Chem. Soc. 1970, 92, 741.
66. (a) Negishi, E.-I.; Okukado, N.; King, A. O.; Van Horn, D. E.; Spiegel, B. I. J. Am. Chem. Soc. 1978, 100, 2254.
67. (b) Panek, J. S.; Hu, T. J. Org. Chem. 1997, 62, 4912.
68. (c) Panek, J. S.; Hu, T. J. Org. Chem. 1997, 62, 4914.
69. (a) Wipf, P.; Jahn, H. Tetrahedron 1996, 52, 12853.
70. (b) Schwartz, J.; Labinger, J. A. Angew. Chem., Int. Ed. Engl. 1976, 15, 333.
71. Negishi, E.; Okukado, N.; Lovich, S. F.; Luo, F.-T. J. Org. Chem. 1984, 49, 2629.
72. The (S)-stereochemistry was assigned based on well-established literature precedence; see ref 53 and Wipf, P.; Kim, Y.; Fritch, P. C. J. Org. Chem. 1993, 58, 7195. Comparison of the molar rotation angle of (S)-5, +23.5, to that of the independently assigned structurally closely related compound 11, +25.9, in the latter paper provides further proof for our assignment of the (S)-configuration of the α-methylation product.
73. Wipf, P.; Lim, S. Angew. Chem., Int. Ed. Engl. 1993, 32, 1068.
74. Erker, G.; Aulbach, M.; Knickmeier, M.; Winghermühle, D.; Krüger, C.; Nolte, M.; Werner, S. J. Am. Chem. Soc. 1993, 1215, 4590.
75. The %ee was assigned by chiral HPLC with a Chiracel OD column.
76. The water effect in the asymmetric methylalumination of alkenes is a generally useful modification that not only provided considerable rate acceleration but in some cases also increased enantioselectivities: Wipf, P.; Ribe, S. To be submitted for publication.
77. D of diol 19, the %ee of the conversion of 6 to 18 proceeded in 80-82%, in good agreement with the HPLC study. Veith, H. J.; Collas, M.; Zimmer, R. Liebigs Ann. Org. Bioorg. Chem. 1997, 391.
78. Levin, J. I.; Turos, E.; Weinreb, S. M. Synth. Commun., 1982, 12, 989.
79. (a) Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
80. (b) Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
81. Archelas, A.; Furstoss, R. J. Org. Chem. 1999, 64, 6112.
82. D values.
83. Horsman, G.; Emeis, C. A. Tetrahedron Lett. 1965, 3037.
84. (a) Forster, L. S.; Moscowitz, A.; Berger, J. G.; Mislow, K. J. Am. Chem. Soc. 1962, 84, 4353.
85. (b) Kirk, D. N. Tetrahedron 1986, 42, 777.
86. (c) Person, R. V.; Monde, K.; Humpf, H.-U.; Berova, N.; Nakanishi, K. Chirality 1995, 7, 128.
87. (d) Dong, J.-G.; Guo, J.; Akritopoulou-Zanze, I.; Kawamura, A.; Nakanishi, K.; Berova, N. Chirality 1999, 11, 707.
88. Unfortunately, we were unable to record the CD spectrum of a natural sample of pitiamide A. Two samples that were generously provided to us by Professor Paul decomposed during shipment from Guam to Pittsburgh.
89. Smith, J. A.; Pease, L. G. CRC Crit. Rev. Biochem. 1980, 8, 315.
90. (a) Gardner, R. R.; Liang, G.-B.; Gellman, S. H. J. Am. Chem. Soc. 1999, 121, 1806.
91. (b) Boussard, G.; Marraud, M. Biopolymers 1979, 18, 1297.
92. (c) Maxfield, F. R.; Leach, S. J.; Stimson, E. R.; Powers, S. P.; Scheraga, H. A. Biopolymers 1980, 18, 2507.
93. 3.
94. Optical rotation values recorded in Table 3 represent the average of three independent measurements. The experimental variations in these three determinations were less than 10% of the average values.
95. Although the vast majority of total syntheses provides optical rotations in good agreement with data reported for the isolated natural product, it is not uncommon that differences arise. See, for example: (a) Edmondson, S.; Danishefsky, S. J.; Sepp-Lorenzino, L.; Rosen, N. J. Am. Chem. Soc. 1999, 121, 2147. (b) Hanessian, S.; Cantin, L.-D.; Andreotti, D. J. Org. Chem. 1999, 64, 4893. (c) McCauley, J. A.; Nagasawa, K.; Lander, P. A.; Mischke, S. G.; Semones, M. A.; Kishi, Y. J. Am. Chem. Soc. 1998, 120, 7647. (d) Wipf, P.; Xu, W. J. Org. Chem. 1996, 61, 6556.
96. Although the vast majority of total syntheses provides optical rotations in good agreement with data reported for the isolated natural product, it is not uncommon that differences arise. See, for example: (a) Edmondson, S.; Danishefsky, S. J.; Sepp-Lorenzino, L.; Rosen, N. J. Am. Chem. Soc. 1999, 121, 2147. (b) Hanessian, S.; Cantin, L.-D.; Andreotti, D. J. Org. Chem. 1999, 64, 4893. (c) McCauley, J. A.; Nagasawa, K.; Lander, P. A.; Mischke, S. G.; Semones, M. A.; Kishi, Y. J. Am. Chem. Soc. 1998, 120, 7647. (d) Wipf, P.; Xu, W. J. Org. Chem. 1996, 61, 6556.
97. Although the vast majority of total syntheses provides optical rotations in good agreement with data reported for the isolated natural product, it is not uncommon that differences arise. See, for example: (a) Edmondson, S.; Danishefsky, S. J.; Sepp-Lorenzino, L.; Rosen, N. J. Am. Chem. Soc. 1999, 121, 2147. (b) Hanessian, S.; Cantin, L.-D.; Andreotti, D. J. Org. Chem. 1999, 64, 4893. (c) McCauley, J. A.; Nagasawa, K.; Lander, P. A.; Mischke, S. G.; Semones, M. A.; Kishi, Y. J. Am. Chem. Soc. 1998, 120, 7647. (d) Wipf, P.; Xu, W. J. Org. Chem. 1996, 61, 6556.
98. Although the vast majority of total syntheses provides optical rotations in good agreement with data reported for the isolated natural product, it is not uncommon that differences arise. See, for example: (a) Edmondson, S.; Danishefsky, S. J.; Sepp-Lorenzino, L.; Rosen, N. J. Am. Chem. Soc. 1999, 121, 2147. (b) Hanessian, S.; Cantin, L.-D.; Andreotti, D. J. Org. Chem. 1999, 64, 4893. (c) McCauley, J. A.; Nagasawa, K.; Lander, P. A.; Mischke, S. G.; Semones, M. A.; Kishi, Y. J. Am. Chem. Soc. 1998, 120, 7647. (d) Wipf, P.; Xu, W. J. Org. Chem. 1996, 61, 6556.
99. The effect of impurities on optical rotation is particularly problematic for small rotation values: Baldwin, J. E.; Hackler, R. E.; Scott, R. M. Chem. Commun. 1969, 1415.
100. For recent examples, see: (a) Beuerle, T.; Engelhard, S.; Bicchi, C.; Schwab, W. J. Nat. Prod. 1999, 62, 35. (b) Van Wagoner, R. M.; Jompa, J.; Tahir, A.; Ireland, C. M. J. Nat. Prod. 1999, 62, 794.
101. For recent examples, see: (a) Beuerle, T.; Engelhard, S.; Bicchi, C.; Schwab, W. J. Nat. Prod. 1999, 62, 35. (b) Van Wagoner, R. M.; Jompa, J.; Tahir, A.; Ireland, C. M. J. Nat. Prod. 1999, 62, 794.