Total synthesis of (-)-ulapualide A: The danger of overdependence on NMR spectroscopy in assignment of stereochemistry

Angewandte Chemie - International Edition

Volumn 46, Issue 23, 2007, Pages 4359-4363

  Pattenden, Gerald ^a   Ashweek, Neil J ^a   Baker Glenn, Charles A G ^a   Walker, Gary M ^a   Yee, James G K ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

Macrocycles; Natural products; Oxazoles; Structure elucidation; Total synthesis

Indexed keywords

MACROCYCLES; NATURAL PRODUCTS; STRUCTURE ELUCIDATION; TOTAL SYNTHESIS;

BIOSYNTHESIS; ISOMERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY;

ORGANIC COMPOUNDS;

OXAZOLE DERIVATIVE; ULAPUALIDE A; UNCLASSIFIED DRUG;

ARTICLE; CHEMISTRY; CONFORMATION; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SENSITIVITY AND SPECIFICITY; STEREOISOMERISM; SYNTHESIS;

MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; OXAZOLES; SENSITIVITY AND SPECIFICITY; STEREOISOMERISM;

EID: 34447265549     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200700459     Document Type: Article

References (45)

1. For leading refereces, see a) S. K. Chattopadhyay, G. Pattenden, Tetrahedron Lett. 1998, 39, 6095-6098;
2. b) S. K. Chattopadhyay, G. Pattenden, J. Chem. Soc. Perkin Trans. 1 2000, 2429-2454.
3. a) S. Matsunaga, C. A. Celatka, N. Fusetani, P. Liu, J. S. Panek, J. Am. Chem. Soc. 1999, 121, 5605-5606;
4. b) P. Liu, J. S. Panek, J. Am. Chem. Soc. 2000, 122, 1235-1236;
5. c) P. Liu, J. S. Panek, J. Am. Chem. Soc. 2000, 122, 11090-11097.
6. a) J. S. Allingham, J. Tanaka, R. King V. A. Klenchin, I. Rayment, G. Marriott, Nat. Struct. Biol. 2003, 10, 1058-1063;
7. b) J. S. Allingham, J. Tanaka, G. Marriott, I. Rayment, Org. Lett. 2004, 6, 597-599.
8. For a synthesis of mycalolide A (2), see Ref. [2].
9. For a review on some incorrectly assigned structures of natural products, see: K. C. Nicolaou, S. A. Synder, Angew. Chem. 2005, 117, 1036-1069;
10. Angew. Chem. Int. Ed. 2005, 44, 1012-1044;
11. diazonamide A is a particularly pertinent example of where X-ray analysis has been misleading; see: J. Li, A. W. G. Burgett, L. Esser, C. Amezcara, P. G. Harran, Angew. Chem. 2001, 113, 4905-4909;
12. Angew. Chem. Int. Ed. 2001, 40, 4770-4773.
13. G. M. Walker, PhD Thesis, University of Nottingham (UK), 2006.
14. a) M. R. Kernan, T. F. Molinski, D. J. Faulkner, J. Org. Chem. 1988, 53, 5014-5020;
15. b) J. Kobayashi, M. Tsuda, H. Fuse, T. Sasaki, Y. Mikami, J. Nat. Prod. 1997, 60, 150-154;
16. c) J. Shin, H.-S. Lee, J.-Y. Kim, H. J Shin, J.-W. Ahn, V. J. Paul, J. Nat. Prod. 2004, 67, 1889-1892.
17. For a model study of this strategy, see: S. K. Chattopadhyay, J. Kempson, A. McNeil, G. Pattenden, M. Reader, D. E. Rippon, D. Waite, J. Chem. Soc. Perkin Trans. 1 2000, 2415-2428.
18. For pertinent details see Ref [1].
19. We thank Dr A. J. Blake for this X-ray analysis.
20. a) C. Alvarez-Ibarra, S. Arias, G. Bañón, M. J. Fernández, M. Rodriguez, V. Sinisterra, J. Chem. Soc. Chem. Commun. 1987, 1509 -1511;
21. b) I. Paterson, K. S. Yeung, J. B. Smaill, Synlett 1993, 774-776.
22. W. M. Pearlman, Tetrahedron Lett. 1967, 8, 1663-1664.
23. Y. Guindon, C. Yoakim, H. E. Morton, J. Org. Chem. 1984, 49, 3912-3920.
24. The oxazole methyl bromide 14 was obtained from (S)-tert-butyl 2-(2-(benzyloxy)acetamido)hydroxypropanoate by cyclization and oxidation using DAST, bromotrichloromethane, and DBU, followed by manipulation of the functionality in the resulting tert-butyl 2-(benzyloxy)methyl)oxazole-4-carboxylate.
25. K. Takai, K. Nitta, O. Fujimura, K. Utimoto, J. Org. Chem. 1989, 54, 4732-4734.
26. a) H. Yoda, T. Shirai, T. Katagiri, K. Takabe, K. Kimata, K. Hosoya, Chem. Lett. 1990, 2037-2038;
27. b) I. Jako, P. Uiber, A. Mann, M. Taddei, C. Wermuth, Tetrahedron Lett. 1990, 31, 1011-1014;
28. c) S. Hanessian, K. Sumi, Synthesis 1991, 1083-1089.
29. a) P. Garner, J. M. Park, J. Org. Chem. 1987, 52, 2361-2364;
30. b) A. McKillop, R. J. K. Taylor, R. J. Watson, N. Lewis, Synthesis 1994, 31-33;
31. c) A. D. Campbell, T. J. Raynham, R. J. K. Taylor, Synthesis 1998, 1707-1709.
32. a) R. Robinson, J. Chem. Soc. 1909, 95, 2167-2174;
33. b) S. Gabriel, Ber. Dtsch. Chem. Ges. 1910, 43, 1283-1287;
34. c) P. Wipf, S. Lim, J. Am. Chem. Soc. 1995, 117, 558-559.
35. The S iodide 22 was obtained from the TBS ether of methyl 6-hydroxy-3-oxohexanoate by asymmetric reduction using (S)-Ru-binap (binap = 2,2′-bis(diphenylphosphanyl)-1,1′-binaphthyl); see: a) M. Kitamura, T. Ohkuma, H. Takaya, R. Noyori, Org. Synth. 1992, 71, 1-13;
36. b) H. Takaya, R. Noyori, Acc. Chem. Res. 1990, 23, 345-350, followed by manipulation of the functionality in the resulting (S)-3-hydroxy hexanoate (> 98.5 % ee).
37. J. Inanaga, K. Hirata, H. Saeki, T. Katsuki, M. Yamaguchi, Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993.
38. a) Y. Hamada, S. Kato, T. Shioiri, Tetrahedron Lett. 1985, 26, 3223-3226;
39. b) M. Sakaitani, Y. Ohfune, Tetrahedron Lett. 1985, 26, 5543-5546;
40. c) M. Sakaitani, Y. Ohfune, J. Org. Chem. 1990, 55, 870-876.
41. L. A. Carpino, J. Am. Chem. Soc. 1993, 115, 4397-4398.
42. A. J. Meyers, D. L. Evans, D. K. Minster, U. Jordis, S. M. Hecht, A. L. Muzzu, J. Org. Chem. 1979, 44, 497-501.
43. See Ref. [8] and also: N. Endoh, K. Tsuboi, R. Kim, Y. Yonezawa, C. Shin, Heterocycles 2003, 60, 1567-1572.
44. For the related steps in our "first-generation" synthesis of structure 3 of ulapualide A, see Ref. [1].
45. J. A. Roesener, P. J. Sheuer, J. Am. Chem. Soc. 1986, 108, 846-847.