Enantioselective total synthesis of marine natural products untenone A and plakevulin A

Synlett

Volumn , Issue 5, 2005, Pages 793-796

  Mizutani, Hirotake ^a   Watanabe, Masayuki ^a   Honda, Toshio ^a  

^a HOSHI UNIVERSITY   (Japan)

Author keywords

DNA polymerase inhibitor; Natural product; Ring closing metathesis; Sharpless asymmetric epoxidation; Total synthesis

Indexed keywords

ALDEHYDE; CARBON; CYCLOPENTENE DERIVATIVE; DNA POLYMERASE INHIBITOR; NATURAL PRODUCT; NUCLEOTIDYLTRANSFERASE INHIBITOR; OCTADECANAL; PLAKEVULIN A; RUTHENIUM; UNCLASSIFIED DRUG; UNTENONE A; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; ENANTIOSELECTIVITY; MARINE ENVIRONMENT; RING CLOSING METATHESIS; SHARPLESS EPOXIDATION; SYNTHESIS;

EID: 15944365188     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-863742     Document Type: Article

References (39)

1. (a) Ishibashi, M.; Takeuchi, S.; Kobayashi, J. Tetrahedron Lett. 1993, 34, 3749.
2. (b) Kobayashi, J. Kagaku To Seibutsu 1993, 31, 659.
3. Saito, F.; Takeuchi, R.; Kamino, T.; Kuramochi, K.; Sugawara, F.; Sakaguchi, K.; Kobayashi, S. Bioorg. Med. Chem. Lett. 2004, 14, 1975.
4. Synthesis of (±)-untenone A, see: (a) Takeda, K.; Nakayama, I.; Yoshii, E. Synlett 1994, 178.
5. (b) Al-Busafi, S.; Whitehead, R. C. Tetrahedron Lett. 2000, 41, 3467.
6. (c) Kuhn, C.; Skaltsounis, L.; Monneret, C.; Florent, J.-C. Eur. J. Org. Chem. 2003, 2585.
7. (d) Chiral synthesis of untenone A, see: Asami, M.; Ishizaki, T.; Inoue, S. Tetrahedron Lett. 1995, 36, 1893.
8. (e) Miyaoka, H.; Watanuki, T.; Saka, Y.; Yamada, Y. Tetrahedron 1995, 51, 8749.
9. Tsuda, M.; Endo, T.; Perpelescu, M.; Yoshida, S.; Watanabe, K.; Fromont, J.; Mikami, Y.; Kobayashi, J. Tetrahedron 2003, 59, 1137.
10. Saito, F.; Takeuchi, R.; Kamino, T.; Kuramochi, K.; Sugawara, F.; Sakaguchi, K.; Kobayashi, S.; Tsuda, M.; Kobayashi, J. Tetrahedron Lett. 2004, 45, 8069.
11. For recent reviews on metathesis, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446.
12. (b) Schrock, R. R. Tetrahedron 1999, 55, 8141.
13. (c) Fürstner, A. Angew. Chem. Int. Ed. 2000, 39, 3013.
14. (d) Trunka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
15. (e) Hoveyda, A. H.; Schrock, R. R. Chem.-Eur. J. 2001, 7, 945.
16. (f) Schrock, R. R.; Hoveyda, A. H. Angew. Chem. Int. Ed. 2003, 42, 4592.
17. (g) Schrock, R. R. J. Mol. Catal. A: Chem. 2004, 213, 21.
18. (h) Schmidt, B. Eur. J. Org. Chem. 2004, 1865.
19. (i) Grubbs, R. H. Tetrahedron 2004, 60, 7117.
20. Mizutani, H.; Watanabe, M.; Honda, T. Tetrahedron 2002, 58, 8929.
21. (a) Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974.
22. (b) For reviews on Sharpless asymmetric epoxidation, see: Finn, M. G.; Sharpless, K. B. In On the Mechanism of Asymmetric Epoxidation with Titanium-Tartrate Catalysts. Asymmetric Synthesis, Vol. 5; Morrison, J. D., Ed.; Academic Press: Tokyo, 1985, 247-308.
23. (c) Pfenninger, A. Synthesis 1986, 89.
24. (d) Shum, W. P.; Cannarsa, M. J. Chirality in Industry II: Developments in the Commercial Manufacture and Applications of Optically Active Compounds; Collins, A. N.; Sheldrake, G. N.; Crosby, J., Eds.; John Wiley & Sons: New York, 1997, 363.
25. Schreiber, J.; Maag, H.; Hashimoto, N.; Eschenmoser, A. Angew. Chem., Int. Ed. Engl. 1971, 10, 330.
26. (a) Luche, J.-L. J. Am. Chem. Soc. 1978, 100, 2226.
27. (b) Gemel, A. L.; Luche, J.-L. J. Am. Chem. Soc. 1981, 103, 5454.
28. (a) Dess, B. D.; Martin, J. C. J. Org. Chem. 1983, 48, 4155.
29. (b) Dess, B. D.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
30. Chini, M.; Crotti, P.; Favero, L.; Macchia, F. Tetrahedron Lett. 1991, 32, 4775.
31. 2Si: C, 73.52; H, 12.34. Found: C, 73.50; H, 12.27.
32. 2Si: C, 72.66; H, 12.20. Found: C, 72.76; H, 12.03.
33. 2Si: C, 73.03; H, 11.75. Found: C, 72.90; H, 11.86.
34. 4: C, 72.59; H, 10.59. Found: C, 72.60; H, 10.74.
35. Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560.
36. Ohkuma, T.; Ooka, H.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 10417.
37. 4: C, 72.21; H, 11.07. Found: C, 72.70; H, 11.20.
38. 4: C, 72.21; H, 11.07. Found: C, 71.96; H, 10.95.
39. The melting point of optically active 2 has not been reported in the literature.