Synthesis of chlamydocin by chelate-Claisen rearrangement

European Journal of Organic Chemistry

Volumn , Issue 3, 2009, Pages 371-377

  Quirin, Christian ^a   Kazmaier, Uli ^a  

^a SAARLAND UNIVERSITY   (Germany)

Author keywords

Aoe; Chlamydocin; Cyclopeptides; Natural products; Rearrangement; Total synthesis

Indexed keywords

EID: 58649110596     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200800890     Document Type: Article

References (75)

1. a) U. Gräfe, Biochemie der Antibiotika, Spektrum, Heidelberg 1992;
2. b) A. E. Eberle, Chimia 1991, 45, 145-153.
3. A. Closse, R. Huguenin, Helv. Chim. Acta 1974, 57, 533-545.
4. a) R. B. Pringle, Plant Physiol. 1970, 46, 45-49;
5. b) M. Kawai, D. H. Rich, J. D. Walton, Biochem. Biophys. Res. Commun. 1983, 111, 398-403;
6. c) S. D. Kim, H. W. Knoche, L. D. Dunkle, D. A. McCrery, K. B. Tomer, Tetrahedron Lett. 1985, 26, 969-972;
7. d) S. Tanis, B. Horenstein, R. Scheffer, J. Rusmussen, Heterocycles 1986, 24, 3424-3431.
8. a) K. Umehara, K. Nakahara, S. Kiyoto, M. Iwami, M. Okamoto, H. Tanaka, M. Kohsaka, H. Aoki, H. J. Imanaka, Antibiot. 1983, 36, 478-483;
9. b) M. Kawai, R. Pottorf, D. H. Rich, J. Med. Chem. 1986, 29, 2409-2411.
10. a) A. Hirota, A. Suzuki, H. Suzuki, S. Tamura, Agric. Biol. Chem. 1973, 37, 643-647;
11. S. Takayama, A. Isogai, M. Nakata, H. Suzuki, A. Suzuki, Agric. Biol. Chem. 1984, 48, 839-842.
12. H. Itazaki, K. Nagashima, K. Sugita, H. Yoshida, Y. Kawamura, Y. Yasuda, K. Matsumoto, K. Ishii, N. Uotani, H. Nakai, A. Terui, S. Yoshimatsu, Y. Ikenishi, Y. Nakagawa, J. Antibiot. 1990, 43, 1524-1532.
13. L. M. Ciuffetti, M. R. Pope, L. D. Dunkle, J. M. Daly, H. W. Knoche, Biochemistry 1983, 22, 3507-3510.
14. S. Gupta, G. Peiser, T. Nakajima, Y. S. Hwang, Tetrahedron Lett. 1994, 35, 6009-6012.
15. W. Gu, M. Cueto, P. R. Jensen, W. Fenical, R. B. Silverman, Tetrahedron 2007, 63, 6535-6541.
16. a) S. B. Singh, D. L. Zink, J. M. Liesch, A. W. Dombrowski, S. J. Darkin-Rattray, D. M. Schmatz, M. A. Goetz, Org. Lett. 2001, 3, 2815-2818;
17. b) S. B. Singh, D. L. Zink, J. M. Liesch, R. T. Mosley, A. W. Dombrowski, G. F. Bills, S. J. Darkin-Rattray, D. M. Schmatz, M. A. Goetz, J. Org. Chem. 2002, 67, 815-825.
18. For reviews on histone deacetylase see: a) A. P. Wolffe, Science 1996, 272, 371-372;
19. b) M. J. Pazin, J. T. Kadonaga, Cell 1997, 89, 325-328;
20. c) C. A. Hassig, J. K. Tong, T. C. Fleischer, T. Owa, P. G. Grable, D. E. Ayer, S. L. Schreiber, Proc. Natl. Acad. Sci. USA 1998, 95, 3519-3524;
21. d) C. M. Grozinger, S. L. Schneider, Proc. Natl. Acad. Sci. USA 2000, 97, 7835-7840;
22. e) B. E. Bernstein, J. K. Tong, S. L. Schneider, Proc. Natl. Acad. Sci. USA 2000, 97, 13708-13713;
23. f) P. T. Meinke, P. Liberator, Curr. Med. Chem. 2001, 8, 211-235.
24. D. H. Rich, J. Singh, J. H. Gardner, J. Org. Chem. 1983, 48, 432-434.
25. D. H. Rich, J. H. Gardner, Tetrahedron Lett. 1983, 24, 5305-5308.
26. D. H. Rich, M. Kawai, Tetrahedron Lett. 1983, 24, 5309-5312.
27. U. Schmidt, A. Lieberknecht, H. Griesser, F. Bartkowiak, Angew. Chem. 1984, 96, 310-311;
28. Angew. Chem. Int. Ed. Engl. 1984, 23, 318-320.
29. R. Jacquier, R. Lazaro, H. Ranirisheno, P. Viallefont, Tetrahedron Lett. 1984, 25, 5525-5528.
30. a) S. Ikegami, T. Hayama, T. Katsuki, M. Yamaguchi, Tetrahedron Lett. 1986, 27, 3403-3406;
31. b) S. Ikegami, H. Uchiyama, T. Hayama, T. Katsuki, M. Yamaguchi, Tetrahedron 1988, 44, 5333-5342.
32. a) J. E. Baldwin, R. M. Adlington, C. R. A. Godfrey, V. K. J. Patel, J. Chem. Soc., Chem. Commun. 1991, 1277-1279;
33. b) J. E. Baldwin, R. M. Adlington, C. R. A. Godfrey, V. K. Patel, Tetrahedron 1993, 49, 7837-7856.
34. J. Taunton, J. L. Collins, S. L. Schreiber, J. Am. Chem. Soc. 1996, 118, 10412-10422.
35. U. Schöllkopf, U. Groth, C. Deng, Angew. Chem. 1981, 93, 793-795;
36. Angew. Chem. Int. Ed. Engl. 1981, 20, 798-799.
37. S. Kim, E.-Y. Kim, H. Ko, Y. H. Jung, Synthesis 2003, 2194-2198.
38. a) P. J. Murray, M. Kranz, M. Ladlow, S. Taylor, F. Berst, A. B. Holmes, K. N. Keavey, A. Jaxa-Chamiec, P. W. Seale, P. Stead, R. J. Uptown, S. L. Croft, W. Clegg, M. R. J. Elsegood, Bioorg. Med. Chem. Lett. 2001, 11, 773-776;
39. b) L. Mou, G. Singh, Tetrahedron Lett. 2001, 42, 6603-6606;
40. c) M. Rodriguez, I. Bruno, E. Cini, M. Marchetti, M. Taddei, L. Gomez-Paloma, J. Org. Chem. 2006, 71, 103-107;
41. d) M. L. Linares, F. J. Agejas, R. Alajarin, J. J. Vaquero, J. Alvarez-Builla, Synthesis 2006, 2069-2073.
42. Reviews: a) U. Kazmaier, Amino Acids 1996, 11, 283-299;
43. b) U. Kazmaier, Liebigs Ann./Recueil 1997, 285-295.
44. a) U. Kazmaier, F. L. Zumpe, Eur. J. Org. Chem. 2001, 4067-4076;
45. b) T. D. Weiß, G. Helmchen, U. Kazmaier, Chem. Commun. 2002, 1270-1271;
46. M. Bauer, U. Kazmaier, Recent Res. Devel. Org. Chem. 2005, 9, 49-69;
47. c) U. Kazmaier, D. Stolz, Angew. Chem. 2006, 118, 3143-3146;
48. Angew. Chem. Int. Ed. 2006, 45, 3072-3075;
49. d) J. Deska, U. Kazmaier, Chem. Eur. J. 2007, 13, 6204-6211.
50. a) U. Kazmaier, Angew. Chem. 1994, 106, 1046-1047;
51. Angew. Chem. Int. Ed. Engl. 1994, 33, 998-999;
52. b) U. Kazmaier, S. Maier, Tetrahedron 1996, 52, 941-995;
53. c) A. Krebs, U. Kazmaier, Tetrahedron Lett. 1996, 37, 7945-7946.
54. a) U. Kazmaier, C. Schneider, Synlett 1996, 975-977;
55. b) U. Kazmaier, C. Schneider, Synthesis 1998, 1321-1326;
56. c) H. Mues, U. Kazmaier, Synlett 2000, 1004-1006.
57. a) U. Kazmaier, S. Maier, J. Org. Chem. 1999, 64, 4574-4575;
58. b) U. Kazmaier, C. Hebach, A. Watzke, S. Maier, H. Mues, V. Huch, Org. Biomol. Chem. 2005, 3, 136-145;
59. c) U. Kazmaier, S. Maier, Org. Lett. 1999, 1, 1763-1766.
60. a) J. Fakstorp, D. Raleigh, L. E. Schniepp, J. Am. Chem. Soc. 1950, 72, 869-874;
61. b) R. G. Parker, J. D. Roberts, W. S. Johnson, L. Werthemann, W. R. Bartlett, T. J. Brocksom, T. T. Li, D. J. Faulkner, M. R. Peterson, J. Am. Chem. Soc. 1970, 92, 741-743.
62. R. J. Kazlauskas, A. N. E. Weissfloch, A. T. Rappaport, L. A. Cuccia, J. Org. Chem. 1991, 56, 2656-2665.
63. A. Mattson, C. Orrenius, N. Ohrner, C. R. Unelius, K. Hult, T. Norin, Acta Chem. Scand. 1996, 50, 918-921.
64. F. Theil, Enzyme in der Organischen Synthese, Spektrum, Heidelberg 1997.
65. In principle the (S,S)-acetate 7, with the "wrong" stereogenic center for the epoxidation, could have been inverted by use of chemical procedures such as oxidation and chiral reduction after cleavage of the acetate functionality to increase the yield of the desired allyl alcohol (S,R)-6. In our case we decided to use (S,S)-7 as a precursor for (S)-Aoda [as present in, for example, apicidine (Figure 1)], the synthesis of which is currently under investigation.
66. U. Schmidt, A. Lieberknecht, H. Griesser, J. Talbiersky, J. Org. Chem. 1982, 47, 3261-3264.
67. Reviews: a) A. Pfenninger, Synthesis 1986, 89-116;
68. b) R. A. Johnson, K. B. Sharpless, Compreh. Org. Synth. 1991, 7, 389-436.
69. a) K. B. Sharpless, R. C. Michaelson, J. Am. Chem. Soc. 1973, 95, 6136-6137;
70. b) K. B. Sharpless, T. R. Verhoeven, Aldrichimica Acta 1979, 12, 63-74.
71. D. B. Dess, J. C. Martin, J. Org. Chem. 1983, 48, 4155-4156.
72. C. Baylon, M.-P. Heck, C. Mioskowski, J. Org. Chem. 1999, 64, 3354-3360.
73. R. W. Woodard, J. Org. Chem. 1985, 50, 4799-4805.
74. D. Crich, K. Sana, S. Guo, Org. Lett. 2007, 9, 4423-4426.
75. R. E. Shute, B. Dunlap, D. H. Rich, J. Med. Chem. 1987, 30, 71-78.