Total synthesis of cis-solamin: Exploiting the RuO4-catalyzed oxidative cyclization of dienes

Organic Letters

Volumn 8, Issue 16, 2006, Pages 3433-3436

  Göksel, Hülya ^a   Stark, Christian B W ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CIS SOLAMIN; CIS-SOLAMIN; FURAN DERIVATIVE; RUTHENIUM DERIVATIVE; RUTHENIUM TETROXIDE;

ANNONACEAE; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

ANNONACEAE; CATALYSIS; CYCLIZATION; FURANS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; RUTHENIUM COMPOUNDS; STEREOISOMERISM;

EID: 33747291925     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060520k     Document Type: Article

References (80)

1. For recent reviews, see: (a) Cavé, A.; Figadère, B.; Laurens, A.; Cortes, D. In Progress in the Chemistry of Organic Natural Products; Herz, W., Kirby, G. W., Moore, R. E., Steglich, W., Tamm, Ch., Eds.; Springer-Verlag: Wien, 1997; Vol. 10, pp 81-288.
2. (b) Alali, F. Q.; Liu, X.-X.; McLaughlin, J. L. J. Nat. Prod. 1999, 62, 504-540.
3. (c) Bermejo, A.; Figadère, B.; Zafra-Polo, M.-C.; Barrachina, I.; Estornell, E.; Cortes, D. Nat. Prod. Rep. 2005, 22, 269-303.
4. (a) Zeng, L.; Ye, Q.; Oberlies, N. H.; Shi, G.; Gu, Z.-M.; He, K. Nat. Prod. Rep. 1996, 13, 276-306.
5. (b) Oberlies, N. H.; Croy, V. L.; Harrison, M. L.; McLaughlin, J. L. Cancer Lett. 1997, 115, 73-79.
6. (c) Oberlies, N. H.; Chang, C.-J.; McLaughlin, J. L. J. Med. Chem. 1997, 40, 2102-2106. See also ref 1.
7. For reviews, see: (a) Hoppe, R.; Scharf, H.-D. Synthesis 1995, 1447-1464.
8. (b) Figadère, B. Acc. Chem. Res. 1995, 28, 359-365.
9. (c) Marshall, J. A.; Hinkle, K. W.; Hagedorn, C. E. Isr. J. Chem. 1997, 37, 97-107.
10. (d) Cassiraghi, G.; Zanardi, F.; Battistini, L.; Rassu, G.; Appendino, G. Chemtracts: Org. Chem. 1998, 11, 803-827.
11. Representative acetogenin total syntheses: (a) Marshall, J. A.; Jiang, H. J. Org. Chem. 1999, 64, 971-975.
12. (b) Bäurle, S.; Hoppen, S.; Koert, U. Angew. Chem. 1999, 111, 1341-1344;
13. Angew. Chem., Int. Ed. 1999, 38, 1263-1266.
14. (c) Sinha, A.; Sinha, S. C.; Sinha, S. C.; Keinan, E. J. Org. Chem. 1999, 64, 2381-2386.
15. (d) Hoppen, S.; Bäurle, S.; Koert, U. Chem. Eur. J. 2000, 6, 2382-2396.
16. (e) Dixon, D. J.; Ley, S. V.; Reynolds, D. J. Angew. Chem. 2000, 112, 3768-3772;
17. Angew. Chem., Int. Ed. 2000, 39, 3622-3626.
18. (f) Harcken, C.; Brückner, R. New J. Chem. 2001, 25, 40-54.
19. (g) Hu, T.-S.; Yu, Q.; Wu, Y.-L.; Wu, Y. J. Org. Chem. 2001, 66, 853-861.
20. (h) Burke, S. D.; Jiang, L. Org. Lett. 2001, 3, 1953-1955.
21. (i) Takahashi, S.; Kubota, A.; Nakata, T. Angew. Chem. 2002, 114, 4945-4948;
22. Angew. Chem., Int. Ed. 2002, 41, 4751-4754.
23. (j) Zhu, L.; Mootoo, D. R. Org. Lett. 2003, 5, 3475-3478.
24. (k) Zhang, Q.; Lu, H.; Richard, C.; Curran, D. P. J. Am. Chem. Soc. 2004, 126, 36-37.
25. (l) Crimmins, M. T.; She, J. J. Am. Chem. Soc. 2004, 126, 12790-12791.
26. (m) Nattrass, G. L.; Diez, E.; McLachlan, M. M.; Dixon, D. J.; Ley, S. V. Angew. Chem. 2005, 117, 586-590;
27. Angew. Chem., Int. Ed. 2005, 44, 580-584.
28. (n) Hanessian, S.; Giroux, S.; Buffat, M. Org. Lett. 2005, 7, 3989-3992.
29. (o) Tinsley, J. M.; Mertz, E.; Chong, P. Y.; Rang, R.-A. F.; Roush, W. R. Org. Lett. 2005, 7, 4245-4248. See also refs 9-11.
30. For a recent review on ruthenium tetroxide catalyzed oxidations, see: Plietker, B. Synthesis 2005, 2453-2472.
31. Roth, S.; Göhler, S.; Cheng, H.; Stark, C. B. W. Eur. J. Org. Chem. 2005, 4109-4118.
32. Representative references for the oxidative cyclization of 1,5-dienes. With ruthenium tetroxide: (a) Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936-3938.
33. (b) Albarella, L.; Musumeci, D.; Sica, D. Eur. J. Org. Chem. 2001, 997-1003.
34. (c) Piccialli, V.; Cavallo, N. Tetrahedron Lett. 2001, 42, 4695-4699.
35. See also ref 6. With potassium permanganate: (d) Klein, E.; Rojahn, W. Tetrahedron 1965, 21, 2353-2358.
36. (e) Walba, D. M.; Wand, M. D.; Wilkes, M. C. J. Am. Chem. Soc. 1979, 101, 4396-4397.
37. (f) Baldwin, J. E.; Crossley, M. J.; Lehtonen, E.-M. M. J. Chem. Soc., Chem. Commun. 1979, 918-920.
38. (g) Kocienski, P. J.; Brown, R. C. D.; Pommier, A.; Procter, M.; Schmidt, B. J. Chem. Soc., Perkin Trans. 1 1998, 9-39.
39. (h) Brown, R. C. D.; Keily, J. F. Angew. Chem. 2001, 113, 4628-4630;
40. Angew. Chem., Int. Ed. 2001, 40, 4496-4498. See also ref 9b and 9c.
41. With osmium tetroxide: (i) de Champdoré, M.; Lasalvia, M.; Piccialli, V. Tetrahedron Lett. 1998, 39, 9781-9784.
42. (j) Donohoe, T. J.; Butterworth: S. Angew. Chem. 2003, 115, 978-981;
43. Angew. Chem., Int. Ed. 2003, 42, 948-951.
44. Gleye, C.; Duret, P.; Laurens, A.; Hocquemiller, R.; Cavé, A. J. Nat. Prod. 1998, 61, 576-579.
45. (a) Makabe, H.; Hattori, Y.; Tanaka, A.; Oritani, T. Org. Lett. 2002, 4, 1083-1085.
46. (b) Cecil, A. R. L.; Brown, R. C. D. Org. Lett. 2002, 4, 3715-3718.
47. (c) Cecil, A. R. L.; Hu, Y. L.; Vicent, M. J.; Duncan, R.; Brown, R. C. D. J. Org. Chem. 2004, 69, 3368-3374.
48. Donohoe, T. J.; Butterworth: S. Angew. Chem. 2005, 117, 4844-4867;
49. Angew. Chem., Int. Ed. 2005, 44, 4766-4768.
50. For syntheses of the natural isomer trans-solamin, see: (a) Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1993, 115, 4891-4892.
51. (b) Trost, B. M.; Shi, Z. P. J. Am. Chem. Soc. 1994, 116, 7459-7460.
52. (c) Makabe, H.; Tanaka, A.; Oritani, T. J. Chem. Soc., Perkin Trans. 1 1994, 1975-1981.
53. (d) Kuriyama, W.; Ishigami, K.; Kitahara, T. Heterocycles 1999, 50, 981-988.
54. (e) Prestat, G.; Baylon, C.; Heck, M.-P.; Grasa, G. A.; Nolan, S. P.; Mioskowski, C. J. Org. Chem. 2004, 69, 5770-5773.
55. For a semi-synthesis of cis- and trans-solamin from Diepomuricanin A, see: Gleye, C.; Franck, X.; Hocquemiller, R.; Laurens, A.; Laprevote, O.; de Barros, S.; Figadère, B. Eur. J. Org. Chem. 2001, 3161-3164.
56. The first two steps of this sequence have previously been described, cf.: Neogi, P.; Doundoulakis, T.; Yazbak, A.; Sinha, S. C.; Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1998, 120, 11279-11284.
57. Zhong, Y.-L.; Shing, T. K. M. J. Org. Chem. 1997, 62, 2622-2624.
58. 2 has previously been suggested to suppress unwanted overoxidation (ref 6). In the case of substrate 6 the addition of this cosolvent proved not necessary.
59. For reviews, see: (a) Theil, F. Chem. Rev. 1995, 95, 2203-2227.
60. (b) Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahedron 1996, 52, 3769-3826.
61. (c) Schmid, R. D.; Verger, R. Angew. Chem. 1998, 110, 1694-1720
62. Angew. Chem., Int. Ed. 1998, 37, 1608-1633.
63. For a review on nonenzymatic desymmetrizations of meso-compounds, see: Willis, M. C. J. Chem. Soc., Perkin Trans. 1 1999, 1765-1784.
64. For a general review on meso-compounds in stereoselective synthesis, see: Hoffmann, R. W. Angew. Chem. 2003, 115, 1128-1142;
65. Angew. Chem., Int. Ed. 2003, 42, 1096-1109.
66. Enzymatic desymmetrizations of THF diols using, e.g., Candida antarctica, Candida rugosa, and Mucor javanicus lipases have been reported previously (ref 17). However, in case of diol 2, these enzymes did not provide substantial amounts of product.
67. For enzymatic desymmetrizations of THF diols, see: (a) Estermann, H.; Prasad, K.; Shapiro, M. Tetrahedron Lett. 1990, 31, 445-448.
68. (b) Naemura, K.; Fukada, R.; Takahashi, N.; Konishi, M.; Hirose, Y. Tetrahedron: Asymmetry 1993, 4, 911-918.
69. (c) Hegemann, K.; Schimanski, H.; Höweler, U.; Haufe, G. Tetrahedron Lett. 2003, 44, 2225-2229.
70. (d) Hegemann, K.; Fröhlich, R.; Haufe, G. Eur. J. Org. Chem. 2004, 2181-2192.
71. For reviews, see: (a) Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639-666.
72. (b) Langer, P. J. Prakt. Chem. 2000, 342, 728-730.
73. For an early publication on the oxidative lactonization of diols using TPAP, see: Bloch, R.; Brillet, C. Synlett 1991, 829-830.
74. MacCoss, R. N.; Balskus; E. P.; Ley, S. V. Tetrahedron Lett. 2003, 44, 7779-7781.
75. (a) Trost, B. M.; Toste, F. D. Tetrahedron Lett. 1999, 40, 7739-7743.
76. (b) Trost, B. M.; Toste, F. D.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067-2096.
77. (c) Trost, B. M.; Frederiksen, M. U.; Rudd, M. T. Angew. Chem. 2005, 117, 6788-6825;
78. Angew. Chem., Int. Ed. 2005, 44, 6630-6666.
79. Trost, B. M.; Müller, T. J. J.; Martinez, J. J. Am. Chem. Soc. 1995, 117, 1888-1899.
80. D = +22 (c = 0.55 in MeOH); see ref 8. For details see also Supporting Information.