Asymmetric synthesis of the mC7N core of the manumycin family: Preparation of (+)-MT 35214 and a formal total synthesis of (-)-alisamycin

Tetrahedron Letters

Volumn 39, Issue 30, 1998, Pages 5433-5436

  Macdonald, Gregor ^a   Alcaraz, Lilian ^a   Lewis, Norman J ^b   Taylor, Richard J K ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 ACETAMIDO 5,6 EPOXY 4 HYDROXY 2 CYCLOHEXEN 1 ONE; ALISAMYCIN; ANTIBIOTIC AGENT; MANUMYCIN; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; EPOXIDATION; METHODOLOGY; STEREOCHEMISTRY;

EID: 0032560709     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01047-8     Document Type: Article

References (34)

1. 1. For a recent review see Besse, P.; Veschambre, H. Tetrahedron 1994, 50, 8885-8927; see also Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622-8623 and references therein.
2. 1. For a recent review see Besse, P.; Veschambre, H. Tetrahedron 1994, 50, 8885-8927; see also Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622-8623 and references therein.
3. 2. For a review see Katsuki, T.; Martin, V. S. Organic Reactions 1996, 48, 1-299.
4. 3. For reviews see Jacobson, E. N. Catalytic Asymmetric Synthesis, (Ed. Ojima, I.), VCH, New York, 1993, 159; Katsuki, T. Coord. Chem Rev. 1995, 140, 189-214.
5. 3. For reviews see Jacobson, E. N. Catalytic Asymmetric Synthesis, (Ed. Ojima, I.), VCH, New York, 1993, 159; Katsuki, T. Coord. Chem Rev. 1995, 140, 189-214.
6. 4. (a) Bentley, P. A.; Bergeron, S.; Cappit, M. W.; Hills, D. E.; Hursthouse, M. B.; Bugent, T. C.; Pulido, R.; Roberts, S. M.; Wu, L. E. Chem Commun. 1997, 739-740.
7. (b) Elston, C. L.; Jackson, R. F. W.; MacDonald, S. J. F.; Murray, P. J. Angew. Chem. Int. Ed. Engl. 1997, 36, 410-412.
8. (c) Bougauchi, M.; Watanabe, S.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1997, 119, 2329-2330.
9. (d) Enders, D.; Zhu, J.; Kramps; L. Liebigs Ann./Recueil 1997, 1101-1113.
10. 5. (a) Wynberg, H.; Marman, B. J. Org. Chem. 1980, 45, 158-161.
11. (b) Baba, N.; Oda, J.; Kauragucki, M. Agric. Biol. Chem. 1986, 50, 3113-3117.
12. (c) Harigaya, Y.; Yamaguchi, H.; Onda, M. Heterocycles 1981, 15, 183-185.
13. (d) For a review see Wynberg, H. Topics in Stereochemistry 1986, 16, 87-129.
14. (e) Lygo, B.; Wainwright, P. G. Tetrahedron Lett. 1998, 39, 1599-1602.
15. 6. Chiral platinum complexes: Baccin, C.; Gusso, A.; Pinna, F.; Strukul, G. Organometallics 1995, 14, 1161-1167; Cyclodextrins: Colonna, S.; Manfredi, A.; Annunziato, R.; Gaggero, N. J. Org. Chem. 1990, 55, 5862-5866; Liposomised mCPBA: Kumar, A.; Bhakuni, V. Tetrahedron Lett. 1996, 37, 4751-4754; Bovine Serum Albumin: Colonna, S.; Gaggero, N.; Manfredi, A.; Spadoni, A. M.; Casella, L.; Cassea, G.; Pasta, P. Tetrahedron 1988, 44, 5169-5178.
16. 6. Chiral platinum complexes: Baccin, C.; Gusso, A.; Pinna, F.; Strukul, G. Organometallics 1995, 14, 1161-1167; Cyclodextrins: Colonna, S.; Manfredi, A.; Annunziato, R.; Gaggero, N. J. Org. Chem. 1990, 55, 5862-5866; Liposomised mCPBA: Kumar, A.; Bhakuni, V. Tetrahedron Lett. 1996, 37, 4751-4754; Bovine Serum Albumin: Colonna, S.; Gaggero, N.; Manfredi, A.; Spadoni, A. M.; Casella, L.; Cassea, G.; Pasta, P. Tetrahedron 1988, 44, 5169-5178.
17. 6. Chiral platinum complexes: Baccin, C.; Gusso, A.; Pinna, F.; Strukul, G. Organometallics 1995, 14, 1161-1167; Cyclodextrins: Colonna, S.; Manfredi, A.; Annunziato, R.; Gaggero, N. J. Org. Chem. 1990, 55, 5862-5866; Liposomised mCPBA: Kumar, A.; Bhakuni, V. Tetrahedron Lett. 1996, 37, 4751-4754; Bovine Serum Albumin: Colonna, S.; Gaggero, N.; Manfredi, A.; Spadoni, A. M.; Casella, L.; Cassea, G.; Pasta, P. Tetrahedron 1988, 44, 5169-5178.
18. 6. Chiral platinum complexes: Baccin, C.; Gusso, A.; Pinna, F.; Strukul, G. Organometallics 1995, 14, 1161-1167; Cyclodextrins: Colonna, S.; Manfredi, A.; Annunziato, R.; Gaggero, N. J. Org. Chem. 1990, 55, 5862-5866; Liposomised mCPBA: Kumar, A.; Bhakuni, V. Tetrahedron Lett. 1996, 37, 4751-4754; Bovine Serum Albumin: Colonna, S.; Gaggero, N.; Manfredi, A.; Spadoni, A. M.; Casella, L.; Cassea, G.; Pasta, P. Tetrahedron 1988, 44, 5169-5178.
19. 7. Gautier, E. C. L.; Lewis, N.; McKillop, A.; Taylor, R. J. K. Tetrahedron Lett. 1994, 35, 8759-8762.
20. 8. Kapfer, I.; Lewis, N. J.; Macdonald, G.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37, 2101-2104.
21. 9. Alcaraz, L.; Macdonald, G.; Kapfer, I.; Lewis, N. J.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37, 6619-6622.
22. 10. Taylor, R. J. K.; Alcaraz, L.; Kapfer-Eyer, I.; Macdonald, G.; Wei, X.; Lewis, N. Synthesis In press.
23. 11. Graham, A. E.; McKerrecher, D.; Davies, D. H.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37, 4457-4460.
24. 12. Graham, A..E.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans, 1 1997, 1087-1089.
25. 13. Alcaraz, L.; Macdonald, G.; Ragot, J. P.; Lewis, N.; Taylor, R. J. K. J. Org. Chem. In press.
26. 14. Wipf, P.; Kim, Y.; Jahn, H. Synthesis 1995, 1549-1561.
27. 15. All new compounds were fully characterised by high field NMR spectroscopy and by elemental analysis and/or HRMS.
28. 16. Ephedrine derived catalysts (Julia, S.; Ginebreda, A.; Guixer, J.; Masana, J.; Tomas, A. J. Chem. Soc., Perkin Trans. 1 1981, 574-577) also catalysed the epoxidation but produced racemic 5.
29. t 28.8 min) followed by recovered 4 (55%).
30. 18. Evans, E.; Kapfer, I.; Macdonald, G.; Lewis, N. J.; Taylor, R. J. K. Synth. Commun. 1997, 27, 1819-1825.
31. 19. Gautier, E. C. L.; Graham, A. E.; McKillop, A.; Standen, S. P.; Taylor, R. J. K. Tetrahedron Lett. 1997, 38, 1881-1884.
32. 20. S. J. Box, M. L. Gilpin, M. Gwynn, G. Hanscomb, S. R. Spear and A. G. Brown, J. Antibiot. 1983, 36, 1631-1637.
33. 21. Chatterjee, S.; Vijayakumar, E. K. S.; Franco, C. M. M.; Blumbach, J.; Ganguli, B. N. J.; Fehlhaber, H. W.; Kogler, H. J. Antibiot. 1993, 46, 1027-1030; Hayashi, K.; Nakagawa, M.; Fujita, T.; Nakayama, M. Biosci. Biotech. Biochem. 1994, 58, 1332-1333.
34. 21. Chatterjee, S.; Vijayakumar, E. K. S.; Franco, C. M. M.; Blumbach, J.; Ganguli, B. N. J.; Fehlhaber, H. W.; Kogler, H. J. Antibiot. 1993, 46, 1027-1030; Hayashi, K.; Nakagawa, M.; Fujita, T.; Nakayama, M. Biosci. Biotech. Biochem. 1994, 58, 1332-1333.