Total asymmetric synthesis of the aphidicolin derivative (11 R)-(-)-8-epi-11-hydroxyaphidicolin using tandem transannular Diels-Alder/aldol reactions

Organic Letters

Volumn 2, Issue 3, 2000, Pages 285-287

  Bélanger, Guillaume ^a   Deslongchamps, Pierre ^a  

^a UNIVERSITÉ DE SHERBROOKE   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; ANTIVIRUS AGENT; APHIDICOLIN; DITERPENE; DRUG DERIVATIVE; ENZYME INHIBITOR;

ACREMONIUM; ARTICLE; CHEMISTRY; STEREOISOMERISM;

ACREMONIUM; ANTINEOPLASTIC AGENTS; ANTIVIRAL AGENTS; APHIDICOLIN; DITERPENES; ENZYME INHIBITORS; STEREOISOMERISM;

EID: 0034628228     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990341l     Document Type: Article

References (34)

1. Brundret, K. M.; Dalziel, W.; Hesp, B.; Jarvis, J. A. J.; Neidle, S. J. J. Chem. Soc., Chem. Commun. 1972, 1027.
2. Ikegami, S.; Taguchi, T.; Ohashi, M.; Oguro, M.; Nagano, H.; Mano, Y. Nature (London) 1978, 275, 458.
3. Dalziel, W.; Hesp, B.; Stevenson, K. M.; Jarvis, J. A. J. J. Chem. Soc., Perkin Trans, 1 1973, 2841.
4. (a) Trost, B. M.; Nishimura, Y.; Yamamoto, K.; McElvain, S. S. J. Am. Chem. Soc. 1979, 101, 1328.
5. (b) McMurry, J.; Andrus, A.; Ksander, G. M.; Musser, J. H.; Johnson, M. A. J. Am. Chem. Soc. 1979, 101, 1330.
6. (c) Corey, E. J.; Tius, M. A.; Das, J. J. Am. Chem. Soc. 1980, 102, 1742.
7. (d) Ireland, R. E.; Godfrey, J. D.; Thaisrivongs, S. J. Am. Chem. Soc. 1981, 103, 2446.
8. (e) Holton, R. A.; Kennedy, R. M.; Kim, H.-B.; Kraft, M. E. J. Am. Chem. Soc. 1987, 109, 1597.
9. (f) Toyota, M.; Nishikawa, Y.; Seishi, T.; Fukumoto, K.; Tetrahedron 1994, 50, 10183.
10. (g) Iwata, C.; Morie, T.; Maezaki, N.; Yamashita, H.; Kuroda, T.; Inoue, T.; Kamei, K.; Imanishi, T.; Tanaka, T.; Kim, S.-W.; Murakami, K. Abstracts of the 32nd Symposium on the Chemistry of Natural Products; 1990.
11. (h) van Tamelen, E. E.; Zawacky, S. R.; Russel, R. K.; Carlson, J. G. J. Am. Chem. Soc. 1983, 105, 142.
12. (i) Bettolo, R. M.; Tagliatesta, P.; Lupi, A.; Bravetti, D. Helv. Chim. Acta 1983, 66, 1922.
13. (j) For a review on the synthesis of aphidicolanes and stemodanes, see Toyota, M.; Ihara, M. Tetrahedron 1999, 55, 5641.
14. (k) Rizzo, C. J.; Smith, A. B., III. Tetrahedron Lett. 1988, 29, 2793.
15. (a) Deslongchamps, P. Pure Appl. Chem. 1991, 24, 23.
16. (b) Hall, D. G.; Caillé, A.-S.; Drouin, M.; Lamothe, S.; Müller, R.; Deslongchamps, P. Synthesis 1995, 1081.
17. (a) Hall, D. G.; Deslongchamps, P. J. Org. Chem., 1995, 60, 7796.
18. (b) McMurry, J. E.; Webb, T. R. J. Med. Chem. 1984, 27, 1367.
19. Toró, A.; Lemelin, C.-A.; Préville, P.; Bélanger, G.; Deslongchamps, P. Tetrahedron 1999, 55, 4655.
20. Takaï, K.; Nitta, K.; Utimoto, K. J. Am. Chem. Soc. 1986, 108, 7408.
21. 2t-Bu, NaH, n-BuLi, NaI, 18-crown-6, THF, r.t, 3h, 85%.
22. (a) Magid, R. M.; Fruchey, O. S.; Johnson, W. L.; Allen, T. G. J. Org. Chem. 1979, 44, 359.
23. (b) Schreiber, S. L.; Meyer, S. D.; Miwa, T.; Nakatsuka, M. J. Org. Chem. 1992, 57, 5058.
24. (a) Beattig, K.; Dallaire, C.; Pitteloud, R.; Deslongchamps, P. Tetrahedron Lett. 1987, 28, 5249.
25. (b) Beattig, K.; Marinier, A.; Pitteloud, R.; Deslongchamps, P. Tetrahedron Lett. 1987, 28, 5253.
26. Elsinger, F. Org. Svnth. 1973, 5, 76.
27. Guindon, Y.; Yoakim, C.; Morton, H. E. J. Org. Chem. 1984, 49, 3912.
28. (a) Niwa, H.; Hida, T.; Yamada, K. Tetrahedron Lett. 1981, 42, 4239.
29. (b) Kuehne, M. E.; Pitner, J. B. J. Org. Chem. 1989, 54, 4553.
30. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
31. The silyl ether and methyl substituents, in positions 3 and 4, respectively, controlled perfectly the diastereoselectivity of the TADA endo transition state, and consequently the two other stereogenic centers formed by the transannular aldol (see ret 6a).
32. Piers, E.; Abeysekera, B. F.; Herbert, D. J.; Suckling, I. D. Can. J. Chem. 1985, 63, 3418.
33. Kovács, G.; Galambos, G.; Juvancz, Z. Synthesis 1977, 171.
34. With an axially oriented hydroxymethyl in C4, the acetonide formation would have inverted ring A from the chair to its boat conformation, which would not indicate the observed coupling constant for the C3 proton.