Asymmetric total synthesis of (-)-callystatin A and (-)-20-epi-callystatin A employing chemical and biological methods

Chemistry - A European Journal

Volumn 8, Issue 18, 2002, Pages 4272-4284

  Enders, Dieter ^a   Vicario, Jose L ^a   Job, Andreas ^a   Wolberg, Michael ^b   Müller, Michael ^b  

^a RWTH AACHEN UNIVERSITY   (Germany)

^b FORSCHUNGSZENTRUM JÜLICH   (Germany)

Author keywords

Asymmetric synthesis; Enzymes hydrazones; Natural products; Total synthesis

Indexed keywords

ALKYLATION; ORGANIC COMPOUNDS; OXIDATION; REDUCTION;

BUILDING BLOCKS;

SYNTHESIS (CHEMICAL);

20 EPICALLYSTATIN A; ALLYL COMPOUND; ANTINEOPLASTIC AGENT; BUTYRALDEHYDE; CALLYSTATIN A; CARBOXYLIC ACID DERIVATIVE; CYTOTOXIC AGENT; DISCODERMOLIDE; EBELACTONE A; HYDRAZONE DERIVATIVE; KETONE DERIVATIVE; LEPTOMYCIN B; NATURAL PRODUCT; PHOSPHONIUM DERIVATIVE; PIRONETIN A; RATJADONE; UNCLASSIFIED DRUG; UNSATURATED FATTY ACID;

ALKYLATION; ANIMAL; ARTICLE; BIOCATALYST; BIOSYNTHESIS; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHEMISTRY; DIASTEREOISOMER; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; OXIDATION REDUCTION REACTION; REDUCTION; SPONGE (PORIFERA); STEREOISOMERISM; SYNTHESIS;

ALKYLATION; ANIMALS; ANTINEOPLASTIC AGENTS; CATALYSIS; FATTY ACIDS, UNSATURATED; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PORIFERA; STEREOISOMERISM;

EID: 0037120192     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20020916)8:18<4272::AID-CHEM4272>3.0.CO;2-K     Document Type: Article

References (78)

1. M. Kobayashi, K. Higuchi, N. Murakami, H. Tajima, S. Aoki, Tetrahedron Lett. 1997, 38, 2859-2862.
2. N. Murakami, W. Wang, M. Aoki, Y. Tsutsui, K. Higuchi, S. Aoki, M. Kobayashi, Tetrahedron Lett. 1997, 38, 5533-5536.
3. N. Murakami. W. Wang, M. Aoki, Y. Tsutsui, M. Sugimoto, M. Kobayashi, Tetrahedron Lett. 1998, 39, 2349-2352.
4. a) N. Murakami, M. Sugimoto, T. Nakajima, M. Kawanishi, Y. Tsutsui, M. Kobayashi, Bioorg. Med. Chem. 2000, 8, 2651-2661;
5. b) N. Murakami, M. Sugimoto, M. Kobayashi, Bioorg. Med. Chem. 2001, 9, 57-67.
6. a) Y. Hayakawa, K. Adachi, N. Komeshima, J. Antibiot. 1987, 40, 1349-1352;
7. b) Y. Hayakawa, K. Sohda, K. Shin-ya, T. Hidaka, H. Seto. J. Antibiot. 1995. 48, 954-961.
8. a) T. Hamamoto, S. Gunji, H. Tsuji, T. Beppu, J. Antibiot. 1983, 36. 639-645;
9. b) T. R. Hurley, R. H. Bunge, N. E. Willer, G. C. Hokanson, J. C. French, J. Antibiot. 1986, 39, 1651-1656;
10. c) J. P. Schaumberg, G. C. Hokanson, J. C. French, J. Chem. Soc. Chem. Commun. 1984, 1450-1452;
11. d) M. Kobayashi, W. Wang, Y. Tsutsui, M. Sugimoto, N. Murakami, Tetrahedron Lett. 1998, 39, 8291-8294.
12. a) I. Umezawa, K. Komiyama, H. Oka, K. Okada, S. Tomisaka, T, Miyano, S. Takano, J. Antibiot. 1984, 37, 706-711;
13. b) K. Komiyama, K. Okada, H. Oka, S. Tomisaka, T. Miyano, S. Funayama, I. Umezawa. J. Antibiot. 1985, 38, 220-223.
14. a) J. B. Tunac, B. D. Graham, W. E. Dobson, J. Antibiot. 1983, 36, 1595-1600;
15. b) S. S. Stampwala, R. H. Bunge, T. R. Hurley, N. E. Willmer, A. J. Brankiewicz, C. E. Steinman, T. A. Smitka, J. C. French, J. Antibiot. 1983, 36, 1601-1605;
16. c) D. L. Boger, S. Ichikawa, W. Zhong, J. Am. Chem. Soc. 2001, 123, 4161-4167.
17. Y. Hayakawa, K. Sohda, H. Seto, J. Antibiot. 1996, 49, 980-984.
18. a) K. Gerth, D. Schummer, G. Höfle, H. Irschik, H. Reichenbach, J. Antibiot. 1995, 48, 973-976;
19. b) D. Schummer, K. Gerth, H. Reichenbach, G. Höfle, Liebigs Ann. 1995, 685-688;
20. c) M. Christmann, U. Bhatt, M. Quitschalle, E. Claus, M. Kalesse, Angew. Chem. 2000, 112, 4535-4538; Angew. Chem. Int. Ed. 2000, 39, 4364-4366;
21. c) M. Christmann, U. Bhatt, M. Quitschalle, E. Claus, M. Kalesse, Angew. Chem. 2000, 112, 4535-4538; Angew. Chem. Int. Ed. 2000, 39, 4364-4366;
22. d) U. Bhatt, M. Christmann, M. Quitschalle, E. Claus, M. Kalesse. J. Org. Chem. 2001, 66, 1885-1893;
23. e) D. R. Williams, D. C. Ihle, S. V. Plummer, Org. Lett. 2001, 3, 1383-1386.
24. a) S. Kobayashi, K. Tsuchiya, T. Harada, M. Nishide, T. Kurokawa, T. Nagakawa, N. Shimada, K. Kobayashi, J. Antibiot. 1994, 47, 697-702;
25. b) S. Kobayashi, K. Tsuchiya, M. Nishide, N. Fakaaki, N. Taizo, S. Nobuyoshi, J. Antibiot. 1995, 48, 893-895;
26. c) M. K. Gurjar, J. T. Henri, D. S. Bose, A. V. R. Rao, Tetrahedron Lett. 1996, 37, 6615-6618;
27. d) M. K. Gurjar, A. Chakrabarti, A. V. R. Rao, Heterocycles 1997, 45, 7-10;
28. e) H. Watanabe, H. Watanabe, T. Kitahara, Tetrahedron Lett. 1998, 39, 8313-8316;
29. f) N. Chida, M. Yoshinaga, T. Tobe, S. Ogawa, Chem. Commun. 1997, 1043-1044;
30. g) G. E. Keck, C. E. Knutson, S. A. Wiles, Org. Lett. 2001, 3, 707-710.
31. a) S. P. Gunasekera, M. Gunasekera, R. E. Longley, G. K. Schulte, J. Org. Chem. 1990, 55, 4912-4915;
32. b) J. B. Nerenberg, D. T. Hung, P. K. Somers, S. L. Schreiber, J. Am. Chem. Soc. 1993, 115, 12621-12622;
33. c) S. L. Schreiber, J. Chen, D. T. Hung, Chem. Biol. 1996, 3, 287-293.
34. a) H. Umezawa, A. Takaaki, K. Uotani, M. Hamada, T. Takeuchi, S. Takahashi, J. Antibiot. 1980, 33, 1594-1596;
35. b) K. Uotani, H. Naganawa, S. Kondo, T. Aoyagi, H. Umezawa, J. Antibiot. 1982, 35, 1495-1499;
36. c) I. Paterson, A. N. Hulme, J. Org. Chem. 1995, 60, 3288-3300.
37. M. T. Crimmins, B. W. King. J. Am. Chem. Soc. 1998, 120, 9084-9085.
38. A. B. Smith III, B. M. Brandt, Org. Lett. 2001, 3, 1685-1688.
39. M. Kalesse, M. Quitschalle, C. P. Khandavalli, A. Saeed, Org. Lett. 2001, 3, 3107-3109.
40. J. A. Marshall, M. P. Bourbeau, J. Org. Chem. 2002, 67, 2751-2754.
41. a) Part of this work has been published in a preliminary form: J. L. Vicario, A. Job, M. Wolberg, M. Müller, D. Enders, Org. Lett. 2002, 4, 1023-1026;
42. b) A. Job, Dissertation, RWTH Aachen (Germany), 2001.
43. a) D. Enders, in Asymmetric Synthesis. Vol. 3 (Ed.: J. D. Morrison), Academic Press, Orlando, 1984, p. 275-339;
44. b) D. Enders, M. Klatt, in Encyclopedia of Reagents for Organic Synthesis, Vol. 1 (Ed.: L. A. Paquette), Wiley, Chichester, 1995, pp. 178-182;
45. c) review: A. Job, C. F. Janeck, W. Bettray, R. Peters, D. Enders, Tetrahedron 2002, 58, 2253-2329.
46. R. Tamura, K. Saegusa, M. Kakihana, D. Oda, J. Org. Chem. 1988, 53, 2723-2728.
47. a) M. Wolberg, W. Hummel, C. Wandrey, M. Müller, Angew. Chem. 2000, 112, 4476-4478; Angew. Chem. Int. Ed. 2000, 39, 4306-4308;
48. a) M. Wolberg, W. Hummel, C. Wandrey, M. Müller, Angew. Chem. 2000, 112, 4476-4478; Angew. Chem. Int. Ed. 2000, 39, 4306-4308;
49. b) M. Wolberg, W. Hummel, M. Müller, Chem. Eur. J. 2001, 7, 4562-4571;
50. A. Job, M. Wolberg, M. Müller, D. Enders, Synlett 2001, 1796-1798.
51. Lactone 10 can also be obtained in >98% ee by diastereoselective reduction of hydroxy keto ester 6 followed by crystallisation and subsequent lactonisation/elimination (see ref. [21b]).
52. J. K. Thottathil, Y. Pendri, W.-S. Li, D. R. Kronenthal. US5278313A, 1994 [Chem. Abstr. 1994, 120, 217699r].
53. F. W. Lichtenthaler, K. Lorenz, W.-Y. Ma, Tetrahedron Lett. 1987. 28, 47-50.
54. The configuration of the newly created stereogenic centre was determined by NOE experiments.
55. D. Enders, L. Wortmann, R. Peters, Acc. Chem. Res. 2000, 33, 157-169.
56. W. C. Still, C. Gennari, Tetrahedron Lett. 1983, 24, 4405-4408.
57. K. Ando, J. Org. Chem. 1997, 62, 1934-1939.
58. R. Appel, Angew. Chem. 1975, 87, 863-874; Angew. Chem. Int. Ed. Engl. 1975, 14, 801-810.
59. R. Appel, Angew. Chem. 1975, 87, 863-874; Angew. Chem. Int. Ed. Engl. 1975, 14, 801-810.
60. 22 fragment of callystatin A: a) J. A. Marshall, R. N. Fitzgerald, J. Org. Chem. 1999, 64, 4477-4481; b) L. C. Dias, P. R. R. Meira, Tetrahedron Lett. 2002, 43, 185-187.
61. 22 fragment of callystatin A: a) J. A. Marshall, R. N. Fitzgerald, J. Org. Chem. 1999, 64, 4477-4481; b) L. C. Dias, P. R. R. Meira, Tetrahedron Lett. 2002, 43, 185-187.
62. A. Job, R. Nagelsdiek, D. Enders, Collect. Czech. Chem. Commun. 2000, 65, 524-538.
63. For the use of ketone 8 in the synthesis of polypropionate chains see: I. Paterson, Pure Appl. Chem. 1992, 64, 1821-1830 and references therein.
64. II-mediated aldol reactions see: c) T. Mukaiyama, N. Iwasawa, R. W. Stevens, T. Haga, Tetrahedron 1984, 40, 1381-1390; d) Y. Nagao, Y. Hagiwara, T. Kumagai, M. Ochiai, T. Inoue, K. Hashimoto, E. Fujita, J. Org. Chem. 1986, 51, 2391-2396; e) D. A. Evans, M. DiMare. J. Am. Chem. Soc. 1986, 108, 2476-2478; f) D. A. Evans, A. E. Weber, J. Am. Chem. Soc. 1986, 108, 6757-6761; g) D. A. Evans, J. R. Gage, J. Org. Chem. 1992, 57, 1961-1963.
65. II-mediated aldol reactions see: c) T. Mukaiyama, N. Iwasawa, R. W. Stevens, T. Haga, Tetrahedron 1984, 40, 1381-1390; d) Y. Nagao, Y. Hagiwara, T. Kumagai, M. Ochiai, T. Inoue, K. Hashimoto, E. Fujita, J. Org. Chem. 1986, 51, 2391-2396; e) D. A. Evans, M. DiMare. J. Am. Chem. Soc. 1986, 108, 2476-2478; f) D. A. Evans, A. E. Weber, J. Am. Chem. Soc. 1986, 108, 6757-6761; g) D. A. Evans, J. R. Gage, J. Org. Chem. 1992, 57, 1961-1963.
66. II-mediated aldol reactions see: c) T. Mukaiyama, N. Iwasawa, R. W. Stevens, T. Haga, Tetrahedron 1984, 40, 1381-1390; d) Y. Nagao, Y. Hagiwara, T. Kumagai, M. Ochiai, T. Inoue, K. Hashimoto, E. Fujita, J. Org. Chem. 1986, 51, 2391-2396; e) D. A. Evans, M. DiMare. J. Am. Chem. Soc. 1986, 108, 2476-2478; f) D. A. Evans, A. E. Weber, J. Am. Chem. Soc. 1986, 108, 6757-6761; g) D. A. Evans, J. R. Gage, J. Org. Chem. 1992, 57, 1961-1963.
67. II-mediated aldol reactions see: c) T. Mukaiyama, N. Iwasawa, R. W. Stevens, T. Haga, Tetrahedron 1984, 40, 1381-1390; d) Y. Nagao, Y. Hagiwara, T. Kumagai, M. Ochiai, T. Inoue, K. Hashimoto, E. Fujita, J. Org. Chem. 1986, 51, 2391-2396; e) D. A. Evans, M. DiMare. J. Am. Chem. Soc. 1986, 108, 2476-2478; f) D. A. Evans, A. E. Weber, J. Am. Chem. Soc. 1986, 108, 6757-6761; g) D. A. Evans, J. R. Gage, J. Org. Chem. 1992, 57, 1961-1963.
68. II-mediated aldol reactions see: c) T. Mukaiyama, N. Iwasawa, R. W. Stevens, T. Haga, Tetrahedron 1984, 40, 1381-1390; d) Y. Nagao, Y. Hagiwara, T. Kumagai, M. Ochiai, T. Inoue, K. Hashimoto, E. Fujita, J. Org. Chem. 1986, 51, 2391-2396; e) D. A. Evans, M. DiMare. J. Am. Chem. Soc. 1986, 108, 2476-2478; f) D. A. Evans, A. E. Weber, J. Am. Chem. Soc. 1986, 108, 6757-6761; g) D. A. Evans, J. R. Gage, J. Org. Chem. 1992, 57, 1961-1963.
69. II-mediated aldol reactions see: c) T. Mukaiyama, N. Iwasawa, R. W. Stevens, T. Haga, Tetrahedron 1984, 40, 1381-1390; d) Y. Nagao, Y. Hagiwara, T. Kumagai, M. Ochiai, T. Inoue, K. Hashimoto, E. Fujita, J. Org. Chem. 1986, 51, 2391-2396; e) D. A. Evans, M. DiMare. J. Am. Chem. Soc. 1986, 108, 2476-2478; f) D. A. Evans, A. E. Weber, J. Am. Chem. Soc. 1986, 108, 6757-6761; g) D. A. Evans, J. R. Gage, J. Org. Chem. 1992, 57, 1961-1963.
70. II-mediated aldol reactions see: c) T. Mukaiyama, N. Iwasawa, R. W. Stevens, T. Haga, Tetrahedron 1984, 40, 1381-1390; d) Y. Nagao, Y. Hagiwara, T. Kumagai, M. Ochiai, T. Inoue, K. Hashimoto, E. Fujita, J. Org. Chem. 1986, 51, 2391-2396; e) D. A. Evans, M. DiMare. J. Am. Chem. Soc. 1986, 108, 2476-2478; f) D. A. Evans, A. E. Weber, J. Am. Chem. Soc. 1986, 108, 6757-6761; g) D. A. Evans, J. R. Gage, J. Org. Chem. 1992, 57, 1961-1963.
71. 2 purchased from Aldrich, catalog no. 38812-2.
72. The configuration of the newly created chiral centre was determined by NOE experiments on the corresponding dimethylacetals of diols 5a-b.
73. P. J. Kocienski, G. Cernigliaro, G. Feldstein, J. Org. Chem. 1977, 42, 353-355.
74. D. Enders, P. Fey, H. Kipphardt, Org. Synth. 1987, 65, 173-182.
75. D. Enders, H. Eichenauer, Chem. Ber. 1979, 112, 2933-2960.
76. D. Enders, H. Eichenauer. U. Baus, H. Schubert, K. A. M. Kremer, Tetrahedron 1984, 40, 1345-1359.
77. D. S. Connor, G. W. Klein, G. N. Taylor, Org. Synth. 1974, 52, 16-19.
78. J. D. White, D. L. Bolton, A. P. Dantanarayana, C. M. J. Fox. R. N Hiner, R. W. Jackson. K. Sakuma, U. S. Warrier, J. Am. Chem. Soc. 1995, 117, 1908-1939.