Synthetic studies toward sordarin: Building blocks for the terpenoid core and for analogues thereof

Journal of Organic Chemistry

Volumn 74, Issue 4, 2009, Pages 1587-1597

  Schulé, Arnaud ^a   Liang, Huan ^b   Vors, Jean Pierre ^c   Ciufolini, Marco A ^a,b  

^a UNIVERSITÉ LYON 1   (France)

^b UNIVERSITY OF BRITISH COLUMBIA   (Canada)

^c BAYER AG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BUILDING BLOCKS; CYCLOPENTADIENES; INTRAMOLECULAR DIELS-ALDER REACTIONS; SORDARICIN; SYNTHETIC STUDIES; TARGET MOLECULES; TERPENOID;

CHEMICAL REACTIONS;

ANTIFUNGAL AGENT; NATURAL PRODUCT; SORDARIN; TERPENOID;

ALKYLATION; ANTIFUNGAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; DIELS ALDER REACTION; DRUG ISOLATION; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; SORDARIA ARANEOSA; SORDARIALES; SYNTHESIS;

CARBOXYLIC ACIDS; CYCLOPENTANES; INDENES; NITRILES; OXYGEN; PROTEIN SYNTHESIS INHIBITORS; STEREOISOMERISM; TERPENES;

EID: 64349097111     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801911s     Document Type: Article

References (85)

1. Cf. (a) Rupp, S. Fut. Microbiol. 2007, 2, 141.
2. (b) Klepser, M. E. Pharmacotherapy 2006, 26, 68.
3. Onyewu, C.; Heitman, J. Anti-Infec. Agents Med. Chem. 2007, 6, 3.
4. Richardson, M. D.; Warnock, D. W. Fungal Infection: Diagnosis and Management, 3rd ed.; Blackwell Publishing: Malden, MA, 2003.
5. Cf. Modern Crop Protection Compounds; Kraemer, W.; Schirmer, U., Eds.; Wiley-VCH: Weinheim, Germany, 2007.
6. (a) Hauser, D.; Sigg, H. P. Helv. Chim. Acta 1971, 54, 1178, and references cited thereinRecent review
7. (b) Liang, H. Beilst. J. Org. Chem. 2008, 4, 31.
8. (a) Justice, M. C.; Hsu, M. J.; Tse, B.; Ku, T.; Balkovec, J. M.; Schmatz, D.; Nielsen, J. J. Biol. Chem. 1998, 273, 3148.
9. (b) Capa, L.; Mendoza, A.; Lavandera, J. L.; Gomez de las Heras, F.; Garcia-Bustos, J. F. Antimicrob. Agents Chemother. 1998, 42, 2694.
10. Shastry, M.; Nielsen, J.; Ku, T.; Hsu, M.-J.; Liberator, P.; Anderson, J.; Schmatz, D.; Justice, M. C. Microbiology 2001, 147, 383.
11. (a) Kato, N.; Kusakabe, S.; Wu, X.; Kamitamari, M.; Takeshita, H. J. Chem. Soc., Chem. Commun. 1993, 1002.
12. (b) Mander, L. N.; Thomson, R. J. Org. Lett. 2003, 5, 1321.
13. Mander, L. N.; Thomson, R. J. J. Org. Chem. 2005, 70, 1654.
14. Kitamura, M.; Chiba, S.; Narasaka, K. Chem. Lett. 2004, 33, 942.
15. (e) Chiba, S.; Kitamura, M.; Narasaka, K. J. Am. Chem. Soc. 2006, 128, 6931.
16. Cf (a) Bueno, J. M.; Chicharro, J.; Fiandor, J. M.; Gomez de las Heras, F.; Huss, S. Bioorg. Med. Chem. Lett. 2002, 12, 1697.
17. (b) Serrano-Wu, M. H.; St Laurent, D. R.; Carroll, T. M.; Dodier, M.; Gao, Q.; Gill, P.; Quesnelle, C. A.; Marinier, A.; Mazzucco, C. E.; Regueiro-Ren, A.; Stickle, T. M.; Wu, D.; Yang, H.; Yang, Z.; Zheng, M.; Zoeckler, M. E.; Vyas, D. M.; Balasubramanian, B. N. Bioorg. Med. Chem. Lett. 2003, 13, 1419, and references cited therein.
18. Tse, B.; Balkovec, J. M.; Blazey, C. M.; Hsu, M.-J.; Nielsen, J.; Schmatz, D. Bioors. Med. Chem. Lett. 1998, 8, 2269.
19. Liang, H.; Schüié, A.; Vors, J.-P.; Ciufolini, M. A. Ors. Lett. 2007, 9, 4119.
20. Interest in such compounds was motivated by the results described in ref.
21. The Kato (ref 5a) and Mander (ref 5b) total syntheses of 1 indeed rely on IMDA routes to the terpenoid nucleus.
22. Reviews: (a) Danishefsky, S. Acc. Chem. Res. 1981, 14, 400.
23. (b) Danishefsky, S. J.; DeNinno, M. P. Angew. Chem., Int. Ed. Engl. 1987, 26, 15.
24. Danishefsky, S.; Kitahara, T.; Schuda, P. F. Org. Synth. 1990, Vol. VII, 312.
25. Kodpinid, M.; Siwapinyoyos, T.; Thebtaranonth, Y. J. Am. Chem. Soc. 1984, 106, 4862.
26. Corey, E. J.; Wood, H. B., Jr. J. Am. Chem. Soc. 1996, 118, 11982.
27. Trost, B. M.; Curran, D. P. J. Am. Chem. Soc. 1981, 103, 7380.
28. Lalic, G.; Petrowski, Z.; Galonic, D.; Matovic, R.; Saicic, R. N. Tetrahedron 2001, 57, 583.
29. Best made as detailed by: Clerici, A.; Pastori, N.; Porta, O. Tetrahedron 2001, 57, 217.
30. Crabtree, S. R.; Mander, L. N.; Sethi, P. S. Org. Synth. 1991, 70, 256.
31. TMS and TES silyl ethers underwent desilylation back to the starting enones upon heating in the presence of dienophiles.
32. An MNDO calculation (Hyperchem package) indicated that the LUMO energy of 2-chloroacrylonitrile is about 0.5 eV lower than that of acrylonitrile or acrolein.
33. Adducts 22 and 24 were not fully characterized. For the series of compounds emanating from 22, full characterization occurred at the stage of derivative 28.
34. This would be consequence of the electronic similarity between the cyclopentadienes in question and the Danishefsky diene (ref 11).
35. Bowey, F. A. Nuclear Magnetic Resonance Spectroscopy; Academic Press: New York, NY, 1969.
36. (a) Alder, K. Justus Liebigs Ann 1951, 571, 157. Theoretical study:
37. (b) Imade, M.; Hirao, H.; Omoto, K.; Fujimoto, H. J. Org. Chem. 1999, 64, 6697.
38. 1H NMR. In crude form, it was directly advanced to 32, which was purified and fully characterized.
39. (a) Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925.
40. (b) Beckwith, A. L. J.; Easton, C. J.; Lawrence, T.; Serelis, A. K. Aust. J. Chem. 1983, 36, 545.
41. As anticipated based on the behavior of the sterically similar camphor: Brown, H. C.; Muzzio, J. J. Am. Chem. Soc. 1966, 88, 2811.
42. Pearlman, W. M. Tetrahedron Lett. 1967, 8, 1663.
43. Because of this disappointing outcome, compounds 47 and 48 were not purified to homogeneity or fully characterized.
44. (a) Lightner, D. A.; Flores, M. J.; Crist, B. V.; Gawronski, J. K. J. Org. Chem. 1980, 45, 3518.
45. (b) Schenato, R. A.; dos Santos, E. M.; Tenius, B. S. M.; Costa, P. R. R.; Caracelli, I.; Zukerman-Schpector, J. Tetrahedron: Asymmetry 2001, 12, 579.
46. Frimer, J. J.; Afri, M.; Baumel, S. D.; Gilinsky-Sharon, P.; Rosenthal, Z.; Gottlieb, H. E. J. Org. Chem. 2000, 65, 1807.
47. This reaction furnished instead ketal 51, which was not thoroughly characterized:
48. Because of this failure, compound 54 was not purified to homogeneity or fully characterized.
49. (a) Cuevas, J. C.; Martos, J. L. Tetrahedron Lett. 1998, 39, 8553.
50. (b) Cuevas, J. C.; Lavandera, J. L.; Martos, J. L. Bioorg. Med. Chem. Lett. 1999, 9, 103.
51. (a) Irie, H. Katakawa, J. Tomita, M. Mizuno, Y. Chem. Lett. 1981, 637.
52. 2COCN.
53. Reviews: (a) Ciganek, E. Org. React. 1997, 51, 201.
54. (b) Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811.
55. Awad, L.; Demange, R.; Zhu, Y.-H.; Vogel, P. Carb. Res. 2006, 341, 1235.
56. (a) Koreeda, M.; Liang, Y.; Akagi, H. J. Chem. Soc., Chem. Commun. 1979, 449.
57. (b) Koreeda, M.; Liang, Y. Tetrahedron Lett. 1981, 22, 15.
58. Majetich, G.; Song, J.-S.; Ringold, C.; Nemeth, G. A.; Newton, M. G. J. Org. Chem. 1991, 56, 3973, and refs cited therein.
59. Aggarwal, V. K.; Mereu, A.; Tarver, G. J.; McCague, R. J. Org. Chem. 1998, 63, 7183.
60. ex = 13.1 Hz).
61. Mancuso, A. J.; Swern, D. Synthesis 1981, 3, 165.
62. Protection of 77 as, e.g., a TES ether furnished intermediates that reacted poorly in subsequent steps.
63. Nagata, W.; Yoshioka, M. Org. React. 1984, 25, 255.
64. Gemal, A. L.; Luche, J. L. J. Am. Chem. Soc. 1981, 103, 5454.
65. Atkins, G. M.; Burgess, E. M. J. Am. Chem. Soc. 1968, 90, 4744.
66. The cyclopentadiene unit in 86 lacks an oxygen substituent that might direct formation of the correct regioisomer of the adduct. However, 56 produces 57 only (Scheme 11 and ref 5c). More significantly, 2, 4-pentadienoic acid reacts with acrylic acid to give a cycloadduct that displays vicinal COOH groups (Davalian, D.; Garratt, P.; Koller, W.; Mansuri, M. J. Org. Chem. 1980, 45, 4183). Thus, we anticipated good regioselectivity in the IMDA cyclization of 86.
67. Snyder, H. R.; Poos, G. I. J. Am. Chem. Soc. 1950, 72, 4104.
68. Banert, K.; Koehler, F.; Meier, B. Tetrahedron Lett. 2003, 44, 3781.
69. Cf. (a) Smith, M. B.; March, J. March's Advanced Organic Chemistry, 5th ed.; John Wiley & Sons: New York, NY, 2001; pp 368 ff.
70. Calculations were carried out with the Hyperchem package, available from Hypercube, Inc. (www.hyper.com).
71. Numerical results are provided as Supporting Information.
72. Over a range of temperatures, compound 84 was immune to the action of trialkylsilyl halides/tertiary amines in the presence of Lewis acids) Danishefsky, S.; Kitahara, T. J. Am. Chem. Soc. 1974, 96, 7807), trialkylsilyl triflates (Review: Bach, T.; Brummerhop, H. J. Prak. Chem. 1999, 341, 410), bis(trimethylsilyl) acetamide (Cameron, D. W.; Feutrill, G. I.; Perlmutter, P. Tetrahedron Lett. 1981, 22, 3273), bis(trimethylsilyl) trifluoroacetamide ( Fattori, D.; de Gucht-eneere, E.; Vogel, P. Tetrahedron Lett. 1989, 30, 7415), or TMSI/HMDS ( Miller, R. D.; McKean, D. R. Synthesis 1979, 73.
73. Corey, E. J.; Gross, A. W. Tetrahedron Lett. 1984, 25, 495.
74. Hosokawa, T.; Aoki, S.; Murahashi, S. Synthesis 1992, 558.
75. (a) Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734.
76. (b) Baldwin, J. E.; Thomas, R. C.; Kruse, L. I.; Silberman, L. J. Org. Chem. 1977, 42, 3846.
77. Hall, P. L.; Gilchrist, J. H.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 9571.
78. (a) Seebach, D. Angew. Chem., Int. Ed. Engl. 1988, 27, 1624.
79. (b) Jackman, L. M.; Rakiewicz, E. F. J. Am. Chem. Soc. 1991, 113, 1202.
80. Bunn, B. J.; Simpkins, N. S. J. Org. Chem. 1993, 58, 533.
81. Lipshutz, B. H.; Wood, M. R.; Lindsley, C. W. Tetrahedron Lett. 1995, 36, 4385.
82. (e) Pratt, L. M.; Newman, A.; St. Cyr, J.; Johnson, H.; Miles, B.; Lattier, A.; Austin, E.; Henderson, S.; Hershey, B.; Lin, M.; Balamraju, Y.; Sammonds, L.; Cheramie, J.; Karnes, J.; Hymel, E.; Woodford, B.; Carter, C. J. Org. Chem. 2003, 68, 6387.
83. A significant excess of Li-base was essential in the present case, even though excess base may actually inhibit enolization, at least in the case of esters: Sun, X.; Collum, D. B. J. Am. Chem. Soc. 2000, 122, 2452.
84. The corresponding TMS enol ether was too labile, while the TES enol ether afforded poor yields in the subsequent IMDA.
85. 3 solutions and IR spectra were obtained from thin films deposited on NaCl plates. More detailed experimental protocols are provided as Supporting Information.