A Strategy for Synthesis of Conduritols and Related Cyclitols via Stereodivergent Vinylsilane-Aldehyde Cyclizations

Journal of Organic Chemistry

Volumn 56, Issue 17, 1991, Pages 5010-5012

  McIntosh, Matthias C ^a   Weinreb, Steven M ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CONDURITOL A; CONDURITOL C; POLYOL; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0025744177     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00017a005     Document Type: Article

References (32)

1. Posternak, T. The Cyclitols; Holden-Day: San Francisco, 1965.
2. Michell, R. H. Biochem. Soc. Trans. 1989, 17, 1.
3. Balci, M.; Sütbeyaz, Y.; Seçen, H. Tetrahedron 1990, 46, 3715.
4. Rinehart, K. L., Jr.; Suomi, T., Eds. Aminocyclitol Antibiotics, ACS Symposium Series 125, American Chemical Society: Washington, D. C., 1980.
5. Atsumi, S.; Umezawa, K.; Iinuma, H.; Naganawa, H.; Nakamura, H.; Iitaka, Y.; Takeuchi, T. J. Antibiot. 1989, 43, 49.
6. Chida, N.; Yamada, K.; Ogawa, S. J. Chem. Soc., Chem. Commun. 1991, 588.
7. Ogawa, S.; Chida, N.; Ohtsuka, M.; Nakazawa, K. J. Org. Chem. 1991, 56, 2976.
8. Jaramillo, C.; Femandes de la Pradilla, R.; Martin-Lomas, M. Carbohydr. Res. 1991, 209, 296.
9. Le Drian, C.; Vionnet, J.-P.; Vogel, P. Helv. Chim. Acta 1990, 73, 161 and references cited therein.
10. Blattner, R.; Ferrier, R. J. J. Chem. Soc., Chem. Commun. 1987, 1008 and references cited therein.
11. Kallmerten, J.; Thompson, R. C. J. Org. Chem. 1990, 55, 6076.
12. Carless, H. A. J.; Oak, O. Z. J. Chem. Soc., Chem. Commun. 1991, 61.
13. Hudlicky, T.; Price, J. D.; Rulin, F.; Tsunoda, T. J. Am. Chem. Soc. 1990, 112, 9439.
14. Ley, S.; Parra, M.; Redgrave, A. J.; Sterfeld, F. Tetrahedron 1990, 46, 4995.
15. Paulsen, H.; Röben, W.; Heiker, F. R. Chem. Ber. 1981, 114, 3242.
16. Barton, D. H. R.; Dalko, P.; Gero, S. D. Tetrahedron Lett. 1991, 32, 2471.
17. van Es, T.; Blumberg, K.; Fuccello, A. Carbohydr. Res. 1977, 59, 361.
18. Speziale, A. J.; Ratta, K. W. J. Am. Chem. Soc. 1962, 84, 864.
19. Levas, E.; Raulet, C. Bull. Soc. Chim. Fr. 1971, 71, 2598.
20. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 3769.
21. Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1991, 56, 3211.
22. Nishigaichi, Y.; Takuwa, A.; Jodai, A. Tetrahedron Lett. 1991, 2383.
23. Yamada, J.-I.; Abe, H.; Yamamoto, Y. J. Am. Chem. Soc. 1990, 112, 6118.
24. Nakai, T.; Mikami, K.; Kawamoto, K.; Loh, T.-P. J. Chem. Soc., Chem. Commun. 1990, 1161.
25. Reusch, W.; Tou, J. S. J. Org. Chem. 1980, 45, 6012.
26. Cambie, R. C.; Renner, N. D.; Rutledge, P. S.; Woodgate, P. D. Synth. Commun. 1989, 19, 537.
27. Overman, L. E.; Bhimenkopf, T. A. Chem. Rev. 1986, 86, 867.
28. Fleming, I.; Dunogues, J.; Smithers, R. Org. React. 1989, 37, 67.
29. Tius, M. A.; Ali, S. J. Org. Chem. 1982, 47, 3163.
30. Hoflack, J.; De Clerq, P. J. Bull. Soc. Chim. Belg. 1983, 92, 407.
31. Fleming, I.; Chow, H.-F. J. Chem. Soc., Perkin Trans. 1 1984, 1816.
32. Tius, M. A. Tetrahedron Lett. 1981, 22, 3335.