Enantioselective synthesis of neocarzinostatin chromophore aglycon

Journal of the American Chemical Society

Volumn 118, Issue 41, 1996, Pages 10006-10007

  Myers, Andrew G ^a   Hammond, Marlys ^a   Wu, Yusheng ^a   Xiang, Jia Ning ^a   Harrington, Philip M ^a   Kuo, Elaine Y ^a  

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ZINOSTATIN CHROMOPHORE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS;

EID: 0029956497     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9618863     Document Type: Article

References (30)

1. (a) Shoji, J. J. Antibiot. 1961, 14, 27.
2. (b) Ishida, N.; Miyazaki, K.; Kumagai, K.; Rikimaru, M. J. Antibiot. 1965, 18, 68.
3. (c) Napier, M. A.; Holmquist, B.; Strydom, D. J.; Goldberg, I. H. Biochem. Biophys. Res. Commun. 1979, 89, 635.
4. (d) Koide, Y.; Ishii, F.; Hasuda, K.; Koyama, Y.; Edo, K.; Katamine, S.; Kitame, F.; Ishida, N. J. Antibiot. 1980, 33, 342.
5. For chromophore structure, see: (a) Edo, K.; Mizugaki, M.; Koide, Y.; Seto, H.; Furihata, K.; Otake, N.; Ishida, N. Tetrahedron Lett. 1985, 26, 331. For carbohydrate stereochemistry, see: (b) Edo, K.; Akiyama, Y.; Saito, K.; Mizugaki, M.; Koide, Y.; Ishida, N. J. Antibiot. 1986, 39, 1615. For chromophore stereochemistry, see: (c) Myers, A. G.; Proteau, P. J.; Handel, T. M. J. Am. Chem. Soc: 1988, 110, 7212.
6. For chromophore structure, see: (a) Edo, K.; Mizugaki, M.; Koide, Y.; Seto, H.; Furihata, K.; Otake, N.; Ishida, N. Tetrahedron Lett. 1985, 26, 331. For carbohydrate stereochemistry, see: (b) Edo, K.; Akiyama, Y.; Saito, K.; Mizugaki, M.; Koide, Y.; Ishida, N. J. Antibiot. 1986, 39, 1615. For chromophore stereochemistry, see: (c) Myers, A. G.; Proteau, P. J.; Handel, T. M. J. Am. Chem. Soc: 1988, 110, 7212.
7. For chromophore structure, see: (a) Edo, K.; Mizugaki, M.; Koide, Y.; Seto, H.; Furihata, K.; Otake, N.; Ishida, N. Tetrahedron Lett. 1985, 26, 331. For carbohydrate stereochemistry, see: (b) Edo, K.; Akiyama, Y.; Saito, K.; Mizugaki, M.; Koide, Y.; Ishida, N. J. Antibiot. 1986, 39, 1615. For chromophore stereochemistry, see: (c) Myers, A. G.; Proteau, P. J.; Handel, T. M. J. Am. Chem. Soc: 1988, 110, 7212.
8. Kappen, L. S.; Napier, M. A.; Goldberg, I. H. Proc. Nat. Acad. Sci. U.S.A. 1980, 77, 1970.
9. (a) Myers, A. G.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1991, 113, 694.
10. (b) Myers, A. G.; Harrington, P. M.; Kwon, B.-M. J. Am. Chem. Soc: 1992, 114, 1086.
11. For the first synthesis of the highly unstable carbocyclic skeleton of 1, see: (a) Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. For leading references to synthetic studies of 1, see: (b) Takahashi, T.; Tanaka, H.; Hirai, Y.; Doi, T.; Yamada, H.; Shiraki, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1993, 32, 1657. (c) Nakatani, K.; Arai, K.; Terashima, S. Tetrahedron 1993, 49, 1901. (d) Kawata, S.; Oishi, T.; Hirama, M. Tetrahedron Lett. 1994, 35, 4595, (e) Wender, P. A.; Tebbe, M. J. Tetrahedron 1994, 50, 1419. (f) Eckhardt, M.; Brückner, R.; Suffert, J. Tetrahedron Lett. 1995, 36, 5167. (g) Toshima, K.; Ohta, K.; Yanagawa, K.; Kano, T.; Nakata, M.; Kinoshita, M.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 10825. (h) Matsumoto, Y.; Kuwatani, Y.; Ueda, I. Tetrahedron Lett. 1995, 36, 3197. (i) Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, J. Tetrahedron 1996, 52, 6283.
12. For the first synthesis of the highly unstable carbocyclic skeleton of 1, see: (a) Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. For leading references to synthetic studies of 1, see: (b) Takahashi, T.; Tanaka, H.; Hirai, Y.; Doi, T.; Yamada, H.; Shiraki, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1993, 32, 1657. (c) Nakatani, K.; Arai, K.; Terashima, S. Tetrahedron 1993, 49, 1901. (d) Kawata, S.; Oishi, T.; Hirama, M. Tetrahedron Lett. 1994, 35, 4595, (e) Wender, P. A.; Tebbe, M. J. Tetrahedron 1994, 50, 1419. (f) Eckhardt, M.; Brückner, R.; Suffert, J. Tetrahedron Lett. 1995, 36, 5167. (g) Toshima, K.; Ohta, K.; Yanagawa, K.; Kano, T.; Nakata, M.; Kinoshita, M.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 10825. (h) Matsumoto, Y.; Kuwatani, Y.; Ueda, I. Tetrahedron Lett. 1995, 36, 3197. (i) Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, J. Tetrahedron 1996, 52, 6283.
13. For the first synthesis of the highly unstable carbocyclic skeleton of 1, see: (a) Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. For leading references to synthetic studies of 1, see: (b) Takahashi, T.; Tanaka, H.; Hirai, Y.; Doi, T.; Yamada, H.; Shiraki, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1993, 32, 1657. (c) Nakatani, K.; Arai, K.; Terashima, S. Tetrahedron 1993, 49, 1901. (d) Kawata, S.; Oishi, T.; Hirama, M. Tetrahedron Lett. 1994, 35, 4595, (e) Wender, P. A.; Tebbe, M. J. Tetrahedron 1994, 50, 1419. (f) Eckhardt, M.; Brückner, R.; Suffert, J. Tetrahedron Lett. 1995, 36, 5167. (g) Toshima, K.; Ohta, K.; Yanagawa, K.; Kano, T.; Nakata, M.; Kinoshita, M.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 10825. (h) Matsumoto, Y.; Kuwatani, Y.; Ueda, I. Tetrahedron Lett. 1995, 36, 3197. (i) Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, J. Tetrahedron 1996, 52, 6283.
14. For the first synthesis of the highly unstable carbocyclic skeleton of 1, see: (a) Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. For leading references to synthetic studies of 1, see: (b) Takahashi, T.; Tanaka, H.; Hirai, Y.; Doi, T.; Yamada, H.; Shiraki, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1993, 32, 1657. (c) Nakatani, K.; Arai, K.; Terashima, S. Tetrahedron 1993, 49, 1901. (d) Kawata, S.; Oishi, T.; Hirama, M. Tetrahedron Lett. 1994, 35, 4595, (e) Wender, P. A.; Tebbe, M. J. Tetrahedron 1994, 50, 1419. (f) Eckhardt, M.; Brückner, R.; Suffert, J. Tetrahedron Lett. 1995, 36, 5167. (g) Toshima, K.; Ohta, K.; Yanagawa, K.; Kano, T.; Nakata, M.; Kinoshita, M.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 10825. (h) Matsumoto, Y.; Kuwatani, Y.; Ueda, I. Tetrahedron Lett. 1995, 36, 3197. (i) Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, J. Tetrahedron 1996, 52, 6283.
15. For the first synthesis of the highly unstable carbocyclic skeleton of 1, see: (a) Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. For leading references to synthetic studies of 1, see: (b) Takahashi, T.; Tanaka, H.; Hirai, Y.; Doi, T.; Yamada, H.; Shiraki, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1993, 32, 1657. (c) Nakatani, K.; Arai, K.; Terashima, S. Tetrahedron 1993, 49, 1901. (d) Kawata, S.; Oishi, T.; Hirama, M. Tetrahedron Lett. 1994, 35, 4595, (e) Wender, P. A.; Tebbe, M. J. Tetrahedron 1994, 50, 1419. (f) Eckhardt, M.; Brückner, R.; Suffert, J. Tetrahedron Lett. 1995, 36, 5167. (g) Toshima, K.; Ohta, K.; Yanagawa, K.; Kano, T.; Nakata, M.; Kinoshita, M.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 10825. (h) Matsumoto, Y.; Kuwatani, Y.; Ueda, I. Tetrahedron Lett. 1995, 36, 3197. (i) Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, J. Tetrahedron 1996, 52, 6283.
16. For the first synthesis of the highly unstable carbocyclic skeleton of 1, see: (a) Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. For leading references to synthetic studies of 1, see: (b) Takahashi, T.; Tanaka, H.; Hirai, Y.; Doi, T.; Yamada, H.; Shiraki, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1993, 32, 1657. (c) Nakatani, K.; Arai, K.; Terashima, S. Tetrahedron 1993, 49, 1901. (d) Kawata, S.; Oishi, T.; Hirama, M. Tetrahedron Lett. 1994, 35, 4595, (e) Wender, P. A.; Tebbe, M. J. Tetrahedron 1994, 50, 1419. (f) Eckhardt, M.; Brückner, R.; Suffert, J. Tetrahedron Lett. 1995, 36, 5167. (g) Toshima, K.; Ohta, K.; Yanagawa, K.; Kano, T.; Nakata, M.; Kinoshita, M.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 10825. (h) Matsumoto, Y.; Kuwatani, Y.; Ueda, I. Tetrahedron Lett. 1995, 36, 3197. (i) Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, J. Tetrahedron 1996, 52, 6283.
17. For the first synthesis of the highly unstable carbocyclic skeleton of 1, see: (a) Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. For leading references to synthetic studies of 1, see: (b) Takahashi, T.; Tanaka, H.; Hirai, Y.; Doi, T.; Yamada, H.; Shiraki, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1993, 32, 1657. (c) Nakatani, K.; Arai, K.; Terashima, S. Tetrahedron 1993, 49, 1901. (d) Kawata, S.; Oishi, T.; Hirama, M. Tetrahedron Lett. 1994, 35, 4595, (e) Wender, P. A.; Tebbe, M. J. Tetrahedron 1994, 50, 1419. (f) Eckhardt, M.; Brückner, R.; Suffert, J. Tetrahedron Lett. 1995, 36, 5167. (g) Toshima, K.; Ohta, K.; Yanagawa, K.; Kano, T.; Nakata, M.; Kinoshita, M.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 10825. (h) Matsumoto, Y.; Kuwatani, Y.; Ueda, I. Tetrahedron Lett. 1995, 36, 3197. (i) Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, J. Tetrahedron 1996, 52, 6283.
18. For the first synthesis of the highly unstable carbocyclic skeleton of 1, see: (a) Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. For leading references to synthetic studies of 1, see: (b) Takahashi, T.; Tanaka, H.; Hirai, Y.; Doi, T.; Yamada, H.; Shiraki, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1993, 32, 1657. (c) Nakatani, K.; Arai, K.; Terashima, S. Tetrahedron 1993, 49, 1901. (d) Kawata, S.; Oishi, T.; Hirama, M. Tetrahedron Lett. 1994, 35, 4595, (e) Wender, P. A.; Tebbe, M. J. Tetrahedron 1994, 50, 1419. (f) Eckhardt, M.; Brückner, R.; Suffert, J. Tetrahedron Lett. 1995, 36, 5167. (g) Toshima, K.; Ohta, K.; Yanagawa, K.; Kano, T.; Nakata, M.; Kinoshita, M.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 10825. (h) Matsumoto, Y.; Kuwatani, Y.; Ueda, I. Tetrahedron Lett. 1995, 36, 3197. (i) Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, J. Tetrahedron 1996, 52, 6283.
19. For the first synthesis of the highly unstable carbocyclic skeleton of 1, see: (a) Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C.; Suffert, J. Tetrahedron Lett. 1988, 29, 909. For leading references to synthetic studies of 1, see: (b) Takahashi, T.; Tanaka, H.; Hirai, Y.; Doi, T.; Yamada, H.; Shiraki, T.; Sugiura, Y. Angew. Chem., Int. Ed. Engl. 1993, 32, 1657. (c) Nakatani, K.; Arai, K.; Terashima, S. Tetrahedron 1993, 49, 1901. (d) Kawata, S.; Oishi, T.; Hirama, M. Tetrahedron Lett. 1994, 35, 4595, (e) Wender, P. A.; Tebbe, M. J. Tetrahedron 1994, 50, 1419. (f) Eckhardt, M.; Brückner, R.; Suffert, J. Tetrahedron Lett. 1995, 36, 5167. (g) Toshima, K.; Ohta, K.; Yanagawa, K.; Kano, T.; Nakata, M.; Kinoshita, M.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 10825. (h) Matsumoto, Y.; Kuwatani, Y.; Ueda, I. Tetrahedron Lett. 1995, 36, 3197. (i) Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, J. Tetrahedron 1996, 52, 6283.
20. Myers, A. G.; Hammond, M.; Wu, Y. Tetrahedron Lett. 1996, 37, 3083.
21. Suzuki, M.; Kawagishi, T.; Noyori, R. Tetrahedron Lett. 1981, 22, 1809.
22. Myers, A. G.; Subramanian, V.; Hammond, M. Tetrahedron Lett. 1996, 37, 587.
23. (a) Zhinkin, D. Y.; Mal'nova, G. N.; Gorislavskaya, Zh. V. Zh. Obshch. Khim. 1968, 38, 2800.
24. (b) Masamune, S.; Ellingboe, J. W.; Choy, W. J. Am. Chem. Soc. 1982, 104, 5526.
25. The stereochemistry of the addition reaction (see 13) was established by the preparation of a cyclic disiloxane derivative, in analogy to ref 3a.
26. Garegg, P. J.; Samuelsson, B. J. Chem. Soc., Chem. Commun. 1979, 978.
27. Although the iodide may be an intermediate in this reaction, it is not observed. For related transformations, see: (a) Mori, K.; Ueda, H. Tetrahedron 1981, 37, 2581. (b) Barluenga, J.; Fernández-Simon, J. L.; Concellón, J. M.; Yus, M. J. Chem. Soc., Perkin Trans. 1 1989, 77. (c) Burke, S. D.; Buchanan, J. L.; Rovin, J. D. Tetrahedron Lett. 1991, 32, 3961.
28. Although the iodide may be an intermediate in this reaction, it is not observed. For related transformations, see: (a) Mori, K.; Ueda, H. Tetrahedron 1981, 37, 2581. (b) Barluenga, J.; Fernández-Simon, J. L.; Concellón, J. M.; Yus, M. J. Chem. Soc., Perkin Trans. 1 1989, 77. (c) Burke, S. D.; Buchanan, J. L.; Rovin, J. D. Tetrahedron Lett. 1991, 32, 3961.
29. Although the iodide may be an intermediate in this reaction, it is not observed. For related transformations, see: (a) Mori, K.; Ueda, H. Tetrahedron 1981, 37, 2581. (b) Barluenga, J.; Fernández-Simon, J. L.; Concellón, J. M.; Yus, M. J. Chem. Soc., Perkin Trans. 1 1989, 77. (c) Burke, S. D.; Buchanan, J. L.; Rovin, J. D. Tetrahedron Lett. 1991, 32, 3961.
30. As further confirmation of structure, the treatment of the aglycon with methyl thioglycolate (0.5 M), triethylamine (0.5 M), and 1,4-cyclohexadiene (1.0 M) in THF at 23 °C afforded a thiol adduct in complete analogy to 1. This adduct has been fully characterized and was obtained in 13% yield (>90% purity, isolated by reverse-phase HPLC). Full details of this reactivity, as well as DNA cleavage by 2, are the subject of a future manuscript.