Catalytic diastereoselective polycyclization of homo(polyprenyl)arene analogues bearing terminal siloxyvinyl groups

Organic Letters

Volumn 8, Issue 24, 2006, Pages 5649-5652

  Uyanik, Muhammet ^a   Ishihara, Kazuaki ^a   Yamamoto, Hisashi ^b  

^a NAGOYA UNIVERSITY   (Japan)

^b UNIVERSITY OF CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

STANNOUS CHLORIDE; TERPENE; TIN DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; CYCLIZATION; STEREOISOMERISM; TERPENES; TIN COMPOUNDS;

EID: 33845984909     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062378t     Document Type: Article

References (23)

1. For reviews, see: (a) Johnson, W. S. Tetrahedron 1991, 47, xi-1.
2. (b) Yoder, R. A.; Johnston, J. N. Chem. Rev. 2005, 105, 4730-4756. To the best of our knowledge, there are no examples of polycyclization of ketals.
3. For our recent contributions, see: (a) Kumazawa, K.; Ishihara, K.; Yamamoto, H. Org. Lett. 2004, 6, 2551-2554.
4. (b) Ishibashi, H.; Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 11122-11123.
5. (c) Uyanik, M.; Ishibashi, H.; Ishihara, K.; Yamamoto, H. Org. Lett. 2005, 7, 1601-1604.
6. (d) Uyanik, M.; Ishihara, K.; Yamamoto, H. Bioorg. Med. Chem. 2005, 13, 5055-5065.
7. Steroid numbering.
8. For Pd(II)-catalyzed polyene cyclizations, see: (a) Koh, J. H.; Mascarenhas, C.; Gagné, M. R. Tetrahedron 2004, 60, 7405-7410.
9. For Hg(II)-catalyzed polyene cyclizations, see: (b) Imagawa, H.; Iyenaga, T.; Nishizawa, M. Org. Lett. 2005, 7, 451-453.
10. 3-trans-10-methylpodocarpatrienol (90% yield; 4β-OH 100% ds), see: Abouabdellah, A.; Bonnet-Delpon, D. Tetrahedron 1994, 50, 11921-11932.
11. 3SiOTf (1 equiv) at -78 °C for 24 h gave 2 (4β-OH 66% ds) and 3 in respective yields of 18% and 10%.
12. 4α- and 4β-Hydroxy polycycles could be separated from each other by column chromatography.
13. Mayr, H.; Kempf, B.; Ofial, A. R. Acc. Chem. Res. 2003, 36, 66-77.
14. 4 (3 equiv) to 4-hydroxypentacycles (49% yield; 4β-OH 84% ds), see: Fish, P. V.; Johnson, W. S. J. Org. Chem. 1994, 59, 2324-2335.
15. 4.
16. For the synclinal preference by Coulomb attractive interaction, see: (a) Seebach, D.; Golinski, J. Helv. Chim. Acta 1981, 64, 1413-1423.
17. (b) Denmark, S. E.; Weber, E. J.; Wilson, T. M.; Wilson, T. M. Tetrahedron 1989, 45, 1053-1065.
18. (c) Yamanaka, M.; Mikami, K. Helv. Chim. Acta 2002, 85, 4264-4271.
19. (a) Rowe, J. W.; Nagasampagi, B. A.; Burgstahler, A. W.; Fitzsimmons, J. W. Phytochemistry 1971, 10, 1647-1651.
20. (b) Lee, C.-K.; Fang, J.-M.; Cheng, Y.-S. Phytochemistry 1995, 39, 391-394.
21. (c) Dakir, M.; El Hanbali, F.; Mellouki, F.; Akssira, A.; Benharref, A.; Quilez Del Moral, J. F.; Barrero, A. F. Nat. Prod. Res. 2005, 19, 719-722.
22. (a) Akita, H.; Otsuka, Y. Japan Kokai Tokkyo Koho, JP51098258 and JP51098267, 1976.
23. (b) Tagat, J. R.; Nazareno, D. V.; Puar, M. S.; McCombie, S. W.; Ganguly, A. K. Bioorg. Med. Chem. Lett. 1994, 4, 1101-1104.