Studies towards diarylheptanoid synthesis. Part 2: Synthesis and ring cleavage reactions of tetrahydro-4H-furo[2,3-b]pyran-2-ones

Tetrahedron Letters

Volumn 44, Issue 33, 2003, Pages 6355-6358

  Cakir, Sidika Polat ^a   Mead, Keith T ^a   Smith, Laura T ^a  

^a MISSISSIPPI STATE UNIVERSITY   (United States)

Author keywords

Blepharocalyxin; C aryl pyranoside; Diarylheptanoid; Oxocarbenium ion

Indexed keywords

HEPTANOIC ACID DERIVATIVE; LEWIS ACID; PYRAN DERIVATIVE;

ADDITION REACTION; ARTICLE; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0041846721     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01421-7     Document Type: Article

References (17)

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3. See the preceding article in this journal, Tetrahedron Letters 2003, 44, 6351.
4. del Rosario-Chow; Ungwitayatorn, J.; Currie, B. L. Tetrahedron Lett. 1991, 32, 1011-1014.
5. D'Annibale A., Trogolo C. Tetrahedron Lett. 35:1994;2083-2086.
6. For examples of stereoselective alkylations of related fused-ring structures, see: Depres J.-P., Greene A.E. J. Org. Chem. 45:1980;2036-2037.
7. For an explanation for this stereoelectronic preference, see: (a) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon: New York, 1983; pp. 209-221. For examples of this type of preferential axial attack, see: (b) Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976-4978; (c) Stewart, A. O.; Williams, R. M. J. Am. Chem. Soc. 1985, 107, 4289; (d) Schmidt, R. R.; Hoffmann, M. Tetrahedron Lett. 1982, 23, 409; (e) Hosomi, A.; Sakata, Y.; Sakurai, H. Tetrahedron Lett. 1984, 25, 2383; (f) Brown, D. S.; Bruno, M.; Davenport, R.; Ley, S. V. Tetrahedron 1989, 45, 4293.
8. For an explanation for this stereoelectronic preference, see: (a) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon: New York, 1983; pp. 209-221. For examples of this type of preferential axial attack, see: (b) Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976-4978; (c) Stewart, A. O.; Williams, R. M. J. Am. Chem. Soc. 1985, 107, 4289; (d) Schmidt, R. R.; Hoffmann, M. Tetrahedron Lett. 1982, 23, 409; (e) Hosomi, A.; Sakata, Y.; Sakurai, H. Tetrahedron Lett. 1984, 25, 2383; (f) Brown, D. S.; Bruno, M.; Davenport, R.; Ley, S. V. Tetrahedron 1989, 45, 4293.
9. For an explanation for this stereoelectronic preference, see: (a) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon: New York, 1983; pp. 209-221. For examples of this type of preferential axial attack, see: (b) Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976-4978; (c) Stewart, A. O.; Williams, R. M. J. Am. Chem. Soc. 1985, 107, 4289; (d) Schmidt, R. R.; Hoffmann, M. Tetrahedron Lett. 1982, 23, 409; (e) Hosomi, A.; Sakata, Y.; Sakurai, H. Tetrahedron Lett. 1984, 25, 2383; (f) Brown, D. S.; Bruno, M.; Davenport, R.; Ley, S. V. Tetrahedron 1989, 45, 4293.
10. For an explanation for this stereoelectronic preference, see: (a) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon: New York, 1983; pp. 209-221. For examples of this type of preferential axial attack, see: (b) Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976-4978; (c) Stewart, A. O.; Williams, R. M. J. Am. Chem. Soc. 1985, 107, 4289; (d) Schmidt, R. R.; Hoffmann, M. Tetrahedron Lett. 1982, 23, 409; (e) Hosomi, A.; Sakata, Y.; Sakurai, H. Tetrahedron Lett. 1984, 25, 2383; (f) Brown, D. S.; Bruno, M.; Davenport, R.; Ley, S. V. Tetrahedron 1989, 45, 4293.
11. For an explanation for this stereoelectronic preference, see: (a) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon: New York, 1983; pp. 209-221. For examples of this type of preferential axial attack, see: (b) Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976-4978; (c) Stewart, A. O.; Williams, R. M. J. Am. Chem. Soc. 1985, 107, 4289; (d) Schmidt, R. R.; Hoffmann, M. Tetrahedron Lett. 1982, 23, 409; (e) Hosomi, A.; Sakata, Y.; Sakurai, H. Tetrahedron Lett. 1984, 25, 2383; (f) Brown, D. S.; Bruno, M.; Davenport, R.; Ley, S. V. Tetrahedron 1989, 45, 4293.
12. For an explanation for this stereoelectronic preference, see: (a) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon: New York, 1983; pp. 209-221. For examples of this type of preferential axial attack, see: (b) Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976-4978; (c) Stewart, A. O.; Williams, R. M. J. Am. Chem. Soc. 1985, 107, 4289; (d) Schmidt, R. R.; Hoffmann, M. Tetrahedron Lett. 1982, 23, 409; (e) Hosomi, A.; Sakata, Y.; Sakurai, H. Tetrahedron Lett. 1984, 25, 2383; (f) Brown, D. S.; Bruno, M.; Davenport, R.; Ley, S. V. Tetrahedron 1989, 45, 4293.
13. For examples, see the preceding article, Tetrahedron Letters 2003, 44, 6351, and: (a) Hosomi, A.; Sakata, Y.; Sakurai, H. Tetrahedron Lett. 1984, 25, 2383; (b) Matsumoto, T.; Katsuki, M.; Suzuki, K. Tetrahedron Lett. 1989, 30, 833-836; (c) Toshima, K.; Matsuo, G.; Ishizuka, T.; Ushiki, Y.; Nakata, M.; Matsumara, S. J. Org. Chem. 1998, 63, 2307-2313; (d) Kaelin, D. E., Jr.; Lopez, O. D.; Martin, S. F. J. Am. Chem. Soc. 2001, 123, 6937-6938.
14. For examples, see the preceding article, Tetrahedron Letters 2003, 44, 6351, and: (a) Hosomi, A.; Sakata, Y.; Sakurai, H. Tetrahedron Lett. 1984, 25, 2383; (b) Matsumoto, T.; Katsuki, M.; Suzuki, K. Tetrahedron Lett. 1989, 30, 833-836; (c) Toshima, K.; Matsuo, G.; Ishizuka, T.; Ushiki, Y.; Nakata, M.; Matsumara, S. J. Org. Chem. 1998, 63, 2307-2313; (d) Kaelin, D. E., Jr.; Lopez, O. D.; Martin, S. F. J. Am. Chem. Soc. 2001, 123, 6937-6938.
15. For examples, see the preceding article, Tetrahedron Letters 2003, 44, 6351, and: (a) Hosomi, A.; Sakata, Y.; Sakurai, H. Tetrahedron Lett. 1984, 25, 2383; (b) Matsumoto, T.; Katsuki, M.; Suzuki, K. Tetrahedron Lett. 1989, 30, 833-836; (c) Toshima, K.; Matsuo, G.; Ishizuka, T.; Ushiki, Y.; Nakata, M.; Matsumara, S. J. Org. Chem. 1998, 63, 2307-2313; (d) Kaelin, D. E., Jr.; Lopez, O. D.; Martin, S. F. J. Am. Chem. Soc. 2001, 123, 6937-6938.
16. For examples, see the preceding article, Tetrahedron Letters 2003, 44, 6351, and: (a) Hosomi, A.; Sakata, Y.; Sakurai, H. Tetrahedron Lett. 1984, 25, 2383; (b) Matsumoto, T.; Katsuki, M.; Suzuki, K. Tetrahedron Lett. 1989, 30, 833-836; (c) Toshima, K.; Matsuo, G.; Ishizuka, T.; Ushiki, Y.; Nakata, M.; Matsumara, S. J. Org. Chem. 1998, 63, 2307-2313; (d) Kaelin, D. E., Jr.; Lopez, O. D.; Martin, S. F. J. Am. Chem. Soc. 2001, 123, 6937-6938.
17. For examples, see the preceding article, Tetrahedron Letters 2003, 44, 6351, and: (a) Hosomi, A.; Sakata, Y.; Sakurai, H. Tetrahedron Lett. 1984, 25, 2383; (b) Matsumoto, T.; Katsuki, M.; Suzuki, K. Tetrahedron Lett. 1989, 30, 833-836; (c) Toshima, K.; Matsuo, G.; Ishizuka, T.; Ushiki, Y.; Nakata, M.; Matsumara, S. J. Org. Chem. 1998, 63, 2307-2313; (d) Kaelin, D. E., Jr.; Lopez, O. D.; Martin, S. F. J. Am. Chem. Soc. 2001, 123, 6937-6938.