Studies in marine macrolide synthesis: Stereocontrolled synthesis of the F-ring subunit of spongistatin 1 (Altohyrtin A).

Tetrahedron Letters

Volumn 38, Issue 32, 1997, Pages 5727-5730

  Paterson, Ian ^a   Keown, Linda E ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIMITOTIC AGENT; MACROLIDE; SPONGISTATIN 1; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030873529     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01257-4     Document Type: Article

References (40)

1. (a) Pettit, G. R.; Cichacz, Z. A.; Gao, F.; Herald, C. L.; Boyd, M. R.; Schmidt, J. M.; Hooper, J. N. A. J. Org. Chem. 1993, 58, 1302.
2. (b) Pettit, G. R.; Cichacz, Z. A.; Gao, F.; Herald, C. L.; Boyd, M. R. J. Chem. Soc., Chem. Commun. 1993, 1166.
3. (c) Pettit, G. R.; Herald, C. L.; Cichacz, Z. A.; Gao, F.; Schmidt, J. M.; Boyd, M. R.; Christie, N. D.; Boettner, F. E. J. Chem. Soc., Chem. Commun. 1993, 1805.
4. (d) Pettit, G. R.; Herald, C. L.; Cichacz, Z. A.; Gao, F.; Boyd, M. R.; Christie, N. D.; Schmidt, J. M. Nat. Prod. Lett. 1993, 3, 239
5. (e) Pettit, G. R.; Cichacz, Z. A.; Herald, C. L.; Gao, F.; Boyd, M. R.; Schmidt, J. M.; Hamel, E.; Bai, R. J. Chem. Soc., Chem. Commun. 1994, 1605.
6. Pettit, G. R. Pure Appl. Chem. 1994, 66, 2271 and references therein.
7. (a) Bai, R.; Cichacz, Z. A.; Herald, C. L.; Pettit, G. R.; Hamel, E. Mol. Pharmacol 1993, 44, 757.
8. (b) Bai, R.; Taylor, G. F.; Cichacz, Z. A.; Herald, C. L.; Kepler, J. A.; Pettit, G. R.; Hamel, E. Biochemistry 1995, 34, 9714.
9. Some of the altohyrtin macrolides reported in the following papers are assumed to be structurally identical to the spongistatins (i.e. altohyrtin A corresponds to spongistatin 1): (a) Kobayashi, M.; Aoki, S.; Sakai, H.; Kawazoe, K.; Kihara, N.; Sasaki, T.; Kitagawa, I. Tetrahedron Lett. 1993, 34, 2795.
10. (b) Kobayashi, M.; Aoki, S.; Sakai, H.; Kihara, N.; Sasaki, T.; Kitagawa, I. Chem. Pharm. Bull. 1993, 41, 989.
11. (c) Kobayashi, M.; Aoki, S.; Kitagawa, I. Tetrahedron Lett. 1994, 35, 1243.
12. (d) Kobayashi, M.; Aoki, S.; Gato, K.; Kitagawa, I. Chem. Pharm. Bull. 1996, 44, 2142.
13. Cinachyrolide A is assumed to be structurally identical to spongistatin 4. Fusetani, N.; Shinoda, K.; Matsunaga, S. J. Am. Chem. Soc. 1993, 115, 3977.
14. Although the absolute configuration at all 24 stereogenic centres in altohyrtin A (≡ spongistatin 1) has been proposed as shown in structure 1 by Kobayashi and Kitagawa (ref 4c,d), this assignment is partially in conflict with the relative stereochemistry proposed independently by the Pettit and Fusetani groups. While we have tentatively accepted structure 1 as a starting point, it is essential to build enough flexibility into the synthetic route in case of later revision of the stereochemical assignment. In particular, access to the enantiomeric relationship for the boxed region in 4 may be required.
15. (a) Paterson, I.; Oballa, R. M.; Norcross, R. D. Tetrahedron Lett. 1996, 37, 8581.
16. See also: (b) Claffey, M. M.; Heathcock, C. H. J. Org. Chem. 1996, 61, 7646.
17. (c) Hayes, C. J.; Heathcock, C. H. J. Org. Chem. 1997, 62, 2678.
18. For a review on marine macrolide synthesis, see: Norcross, R. D.; Paterson, I. Chem. Rev. 1995, 95, 2041.
19. +630.3858, found 630.3860.
20. (a) Paterson, I.; Nowak, T. Tetrahedron Lett. 1996, 37, 8243.
21. (b) Paterson, I.; Tillyer, R. D. J. Org. Chem. 1993, 58, 4182.
22. Cowden, C. J.; Paterson, I. Org. React. 1997, 51, in press.
23. Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560.
24. This level of selectivity is in accord with results reported by Evans et al. (ref 12) for similar reductions of α-benzyloxy-β-hydroxy kctones. In related systems to 9, we have found that replacement of the benzyl ether by a TBS ether can lead to improved stereoselectivity.
25. (a) Rychnovsky, S. D.; Skalitzky, D. J. Tetrahedron Lett. 1990, 31, 945.
26. (b) Rychnovsky, S. D.; Rogers, B.; Yang, G. J. Org. Chem. 1993, 58, 3511.
27. (c) Evans, D. A.; Rieger, D. L.; Gage, J. R. Tetrahedron Lett. 1990, 31, 7099.
28. (a) Oikawa, Y.; Yoshioka, T.; Yonemitsu, O. Tetrahedron Lett. 1982, 23, 885.
29. (b) Horita, K.; Yoshioka, T.; Tanaka, T.; Oikawa, Y.; Yonemitsu, O. Tetrahedron 1986, 42, 3021.
30. Blanchelte, M. A.; Choy, W.; Davis, J. T.; Esscnfeld, A. P.; Masamune, S.; Roush, W.R.; Sakai, T. Tetrahedron Lett. 1984, 25, 2183.
31. (a) Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768.
32. (b) Wang, Z. -M.; Sharpless, K. B. Tetrahedron Lett. 1993, 34, 8225.
33. (c) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
34. Lipshutz, B. H.; Pegram, J. J. Tetrahedron Lett. 1980, 21, 3343.
35. (a) Paterson, I.; Yeung, K. -S.; Smaill, J. B. Synlett 1993, 774.
36. (b) Alvarez-Ibarra, C.; Arias, S.; Banon, G.; Fernandez, M. J.; Rodriguez, M.; Sinisterra, V. J. J. Chem. Soc., Chem. Commun. 1987, 1509.
37. For similar equilibration conditions, as used in the synthesis of halichondrin tetrahydropyrans, see: (a) Aicher, T. D.; Kishi, Y. Tetrahedron Lett. 1987, 28, 3463.
38. (b) Duan, J. J.-W.; Kishi, Y. Tetrahedron Lett. 1993, 34, 7541.
39. (c) Cooper, A. J.; Salomon, R. G. Tetrahedron Lett. 1990, 31, 3813.
40. (d) Burke, S. D.; Jung, K. W.; Phillips, J. R.; Perri, R. E. Tetrahedron Lett. 1994, 35, 703.