Asymmetric synthesis of the left hand portion of the azinomycins

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 7, 1998, Pages 1249-1255

  Bryant, Helen J ^a   Dardonville, Christophe Y ^a   Hodgkinson, Timothy J ^a,b   Hursthouse, Michael B ^c   Malik, K M Abdul ^c   Shipman, Michael ^a,b  

^a LOUGHBOROUGH UNIVERSITY   (United Kingdom)

^b UNIVERSITY OF EXETER   (United Kingdom)

^c CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748830735     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a709084f     Document Type: Article

References (36)

1. (a) K. Nagaoka, M. Matsumoto, J. Ono, K. Yokoi, S. Ishizeki and T. Nakashima, J. Antibiot., 1986, 39, 1527;
2. (b) K. Yokoi, K. Nagaoka and T. Nakashima, Chem. Pharm. Bull., 1986, 34, 4554;
3. (c) S. Ishizeki, M. Ohtsuka, K. Irinoda, K.-I. Kukita, K. Nagaoka and T. Nakashima, J. Antibiot., 1987, 40, 60.
4. M. Hashimoto, M. Matsumoto, K. Yamada and S. Terashima, Tetrahedron Lett., 1994, 35, 2207.
5. R. W. Armstrong, M. E. Salvati and M. Nguyen, J. Am. Chem. Soc., 1992, 114, 3144.
6. W. B. Pratt, R. W. Ruddon, W. D. Ensminger and J. Maybaum, The Amicancer Drugs, Oxford University Press, Oxford, 2nd edn, 1994.
7. For synthetic approaches to the azinomycins, see (a) M. Shibuya and H. Terauchi, Tetrahedron Lett., 1987, 28, 2619;
8. (b) K. Ando, T. Yamada and M. Shibuya, Heterocycles, 1989, 29, 2209;
9. (c) P. England, K. H. Chun, E. J. Moran and R. W. Armstrong, Tetrahedron Lett., 1990, 31, 2669;
10. (d) E. J. Moran and R. W. Armstrong, Tetrahedron Lett., 1991, 32, 3807;
11. (e) R. W. Armstrong, J. E. Tellew and E. J. Moran, J. Org. Chem., 1992, 57, 2208;
12. (j) K. Shishido, T. Omodani and M. Shibuya, J. Chem. Soc., Perkin Trans. 1, 1992, 2053;
13. (g) R. S. Coleman and A. J. Carpenter, J. Org. Chem., 1992, 57, 5813;
14. (h) R. W. Armstrong and E. J. Moran, J. Am. Chem. Soc., 1992, 114, 371;
15. (i) M. Hashimoto, K. Yamada and S. Terashima, Chem. Lett., 1992, 975;
16. (j) R. W. Armstrong, J. E. Tellew, Z. Zhao and E. J. Moran, J. Org. Chem., 1993, 58, 7848;
17. (k) R. S. Coleman and A. J. Carpenter, J. Org. Chem., 1993, 58, 4452;
18. (l) Y. Konda, T. Machida, T. Sasaki, K. Takeda, H. Takayanagi and Y. Harigaya, Chem. Pharm. Bull., 1994, 42, 285;
19. (m) M. Hashimoto and S. Terashima, Chem. Lett., 1994, 1001;
20. (n) M. Hashimoto and S. Terashima, Tetrahedron Lett., 1994, 35, 9409;
21. (o) R. W. Armstrong, J. E. Tellew and E. J. Moran, Tetrahedron Lett., 1996, 37, 447;
22. (p) Y. Konda, T. Machida, M. Akaiwa, K. Takeda and Y. Harigaya, Heterocycles, 1996, 43, 555;
23. (q) H. J. Bryant, C. Y. Dardonville, T. J. Hodgkinson, M. Shipman and A. M. Z. Slawin, Synlett, 1996, 973;
24. (r) R. S. Coleman, C. R. Sarko and J. P. Gittinger, Tetrahedron Lett., 1997, 38, 5917;
25. (s) R. S. Coleman and A. J. Carpenter, Tetrahedron, 1997, 53, 16 313.
26. For a preliminary account of some of this work, see reference 5q.
27. H. C. Kolb, M. S. VanNieuwenhze and K. B. Sharpless, Chem. Rev., 1994, 94, 2483.
28. G. Lhommet, M. G. Richaud and P. Maitte, C. R. Seances Acad. Sci., Ser. C, 1980, 290, 445.
29. During the completion of this work, a paper describing the asymmetric dihydroxylation of benzyl 3,3-dimethylacrylate with AD-mix-β appeared in the literature (H. Shao and M. Goodman, J. Org. Chem., 1996, 61, 2582).
30. T. Katsuki and V. S. Martin, Org. React. (N. Y.), 1996, 48, 1.
31. M. Shibuya, Tetrahedron Lett., 1983, 24, 1175.
32. J. A. Darr, S. R. Drake, M. B. Hursthouse and K. M. A. Malik, Inorg. Chem., 1993, 32, 5704.
33. G. M. Sheldrick, SHELXS86 Program for Crystal Structure Solution, Acta Crystallogr., Sect. A, 1990, 46, 467.
34. G. M. Sheldrick, SHELXL93 Program for Crystal Structure Refinement, University of Gottingen, Germany, 1993.
35. K. Davies, SNOOPI Program for Crystal Structure Drawing, University of Oxford, UK, 1983.
36. M. Onda, Y. Konda, S. Omura and T. Hata, Chem. Pharm. Bull., 1971, 19, 2013.