Studies towards diarylheptanoid synthesis. Part 1: Synthesis and ring cleavage reactions of hexahydro-2H,5H-pyrano[2,3-b]pyran-2-ones

Tetrahedron Letters

Volumn 44, Issue 33, 2003, Pages 6351-6353

  Li, Wei ^a   Mead, Keith T ^a   Smith, Laura T ^a  

^a MISSISSIPPI STATE UNIVERSITY   (United States)

Author keywords

Blepharocalyxin; C aryl pyranoside; Diarylheptanoid; Hexahydro 2H,5H pyrano 2,3 b pyran 2 one; Oxocarbenium ion

Indexed keywords

HEPTANOIC ACID DERIVATIVE; LEWIS ACID; PYRAN DERIVATIVE; PYRANOSIDE;

ARTICLE; DIELS ALDER REACTION; STEREOSPECIFICITY; SUBSTITUTION REACTION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0041346083     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01420-5     Document Type: Article

References (26)

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6. For examples, see: (a) Matsumoto, T.; Katsuki, M.; Suzuki, K. Tetrahedron Lett. 1989, 30, 833-836; (b) Toshima, K.; Matsuo, G.; Ishizuka, T.; Ushiki, Y.; Nakata, M.; Matsumura, S. J. Org. Chem. 1998, 63, 2307-2313; (c) Kaelin, D. E., Jr.; Lopez, O. D.; Martin, S. F. J. Am. Chem. Soc. 2001, 123, 6937-6938. For other strategies in C-aryl pyranoside synthesis, see: (d) Boulineau, F. P.; Wei, A. Org. Lett. 2002, 4, 2281-2283; (e) Palmacci, E. R.; Seeberger, P. H. Org. Lett. 2001, 3, 1547-1550; (f) Steinhuebel, D. P.; Fleming, J. J.; Du Bois, J. D. Org. Lett. 2002, 4, 293-295; (g) Ramnauth, J.; Poulin, O.; Bratovanov, S. S.; Rakhit, S.; Maddaford, S. P. Org. Lett. 2001, 3, 2571-2573.
7. For examples, see: (a) Matsumoto, T.; Katsuki, M.; Suzuki, K. Tetrahedron Lett. 1989, 30, 833-836; (b) Toshima, K.; Matsuo, G.; Ishizuka, T.; Ushiki, Y.; Nakata, M.; Matsumura, S. J. Org. Chem. 1998, 63, 2307-2313; (c) Kaelin, D. E., Jr.; Lopez, O. D.; Martin, S. F. J. Am. Chem. Soc. 2001, 123, 6937-6938. For other strategies in C-aryl pyranoside synthesis, see: (d) Boulineau, F. P.; Wei, A. Org. Lett. 2002, 4, 2281-2283; (e) Palmacci, E. R.; Seeberger, P. H. Org. Lett. 2001, 3, 1547-1550; (f) Steinhuebel, D. P.; Fleming, J. J.; Du Bois, J. D. Org. Lett. 2002, 4, 293-295; (g) Ramnauth, J.; Poulin, O.; Bratovanov, S. S.; Rakhit, S.; Maddaford, S. P. Org. Lett. 2001, 3, 2571-2573.
8. For examples, see: (a) Matsumoto, T.; Katsuki, M.; Suzuki, K. Tetrahedron Lett. 1989, 30, 833-836; (b) Toshima, K.; Matsuo, G.; Ishizuka, T.; Ushiki, Y.; Nakata, M.; Matsumura, S. J. Org. Chem. 1998, 63, 2307-2313; (c) Kaelin, D. E., Jr.; Lopez, O. D.; Martin, S. F. J. Am. Chem. Soc. 2001, 123, 6937-6938. For other strategies in C-aryl pyranoside synthesis, see: (d) Boulineau, F. P.; Wei, A. Org. Lett. 2002, 4, 2281-2283; (e) Palmacci, E. R.; Seeberger, P. H. Org. Lett. 2001, 3, 1547-1550; (f) Steinhuebel, D. P.; Fleming, J. J.; Du Bois, J. D. Org. Lett. 2002, 4, 293-295; (g) Ramnauth, J.; Poulin, O.; Bratovanov, S. S.; Rakhit, S.; Maddaford, S. P. Org. Lett. 2001, 3, 2571-2573.
9. For examples, see: (a) Matsumoto, T.; Katsuki, M.; Suzuki, K. Tetrahedron Lett. 1989, 30, 833-836; (b) Toshima, K.; Matsuo, G.; Ishizuka, T.; Ushiki, Y.; Nakata, M.; Matsumura, S. J. Org. Chem. 1998, 63, 2307-2313; (c) Kaelin, D. E., Jr.; Lopez, O. D.; Martin, S. F. J. Am. Chem. Soc. 2001, 123, 6937-6938. For other strategies in C-aryl pyranoside synthesis, see: (d) Boulineau, F. P.; Wei, A. Org. Lett. 2002, 4, 2281-2283; (e) Palmacci, E. R.; Seeberger, P. H. Org. Lett. 2001, 3, 1547-1550; (f) Steinhuebel, D. P.; Fleming, J. J.; Du Bois, J. D. Org. Lett. 2002, 4, 293-295; (g) Ramnauth, J.; Poulin, O.; Bratovanov, S. S.; Rakhit, S.; Maddaford, S. P. Org. Lett. 2001, 3, 2571-2573.
10. For examples, see: (a) Matsumoto, T.; Katsuki, M.; Suzuki, K. Tetrahedron Lett. 1989, 30, 833-836; (b) Toshima, K.; Matsuo, G.; Ishizuka, T.; Ushiki, Y.; Nakata, M.; Matsumura, S. J. Org. Chem. 1998, 63, 2307-2313; (c) Kaelin, D. E., Jr.; Lopez, O. D.; Martin, S. F. J. Am. Chem. Soc. 2001, 123, 6937-6938. For other strategies in C-aryl pyranoside synthesis, see: (d) Boulineau, F. P.; Wei, A. Org. Lett. 2002, 4, 2281-2283; (e) Palmacci, E. R.; Seeberger, P. H. Org. Lett. 2001, 3, 1547-1550; (f) Steinhuebel, D. P.; Fleming, J. J.; Du Bois, J. D. Org. Lett. 2002, 4, 293-295; (g) Ramnauth, J.; Poulin, O.; Bratovanov, S. S.; Rakhit, S.; Maddaford, S. P. Org. Lett. 2001, 3, 2571-2573.
11. For examples, see: (a) Matsumoto, T.; Katsuki, M.; Suzuki, K. Tetrahedron Lett. 1989, 30, 833-836; (b) Toshima, K.; Matsuo, G.; Ishizuka, T.; Ushiki, Y.; Nakata, M.; Matsumura, S. J. Org. Chem. 1998, 63, 2307-2313; (c) Kaelin, D. E., Jr.; Lopez, O. D.; Martin, S. F. J. Am. Chem. Soc. 2001, 123, 6937-6938. For other strategies in C-aryl pyranoside synthesis, see: (d) Boulineau, F. P.; Wei, A. Org. Lett. 2002, 4, 2281-2283; (e) Palmacci, E. R.; Seeberger, P. H. Org. Lett. 2001, 3, 1547-1550; (f) Steinhuebel, D. P.; Fleming, J. J.; Du Bois, J. D. Org. Lett. 2002, 4, 293-295; (g) Ramnauth, J.; Poulin, O.; Bratovanov, S. S.; Rakhit, S.; Maddaford, S. P. Org. Lett. 2001, 3, 2571-2573.
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14. For examples of related reactions, see: (a) Mootoo, D. R.; Fraser-Reid, B. Carbohydr. Res. 1988, 174, 99-112; (b) Cohen, N.; Schaer, B.; Saucy, G.; Borer, R.; Todaro, L.; Chiu, A.-M. J. Org. Chem. 1989, 54, 3282-3292; (c) Ungureanu, I.; Klotz, P.; Schoenfelder, A.; Mann, A. Tetrahedron Lett. 2001, 42, 6087-6091.
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18. (a) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon: New York, 1983; pp. 209-221. For examples of these reactions, see: (b) Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976-4978; (c) Schmidt, R. R.; Hoffmann, M. Tetrahedron Lett. 1982, 23, 409-412; (d) Hosomi, A.; Sakata, Y.; Sakurai, H. Tetrahedron Lett. 1984, 25, 2383-2386; (e) Brown, D. S.; Bruno, M.; Davenport, R.; Ley, S. V. Tetrahedron 1989, 45, 4293-4308.
19. (a) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon: New York, 1983; pp. 209-221. For examples of these reactions, see: (b) Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976-4978; (c) Schmidt, R. R.; Hoffmann, M. Tetrahedron Lett. 1982, 23, 409-412; (d) Hosomi, A.; Sakata, Y.; Sakurai, H. Tetrahedron Lett. 1984, 25, 2383-2386; (e) Brown, D. S.; Bruno, M.; Davenport, R.; Ley, S. V. Tetrahedron 1989, 45, 4293-4308.
20. (a) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon: New York, 1983; pp. 209-221. For examples of these reactions, see: (b) Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976-4978; (c) Schmidt, R. R.; Hoffmann, M. Tetrahedron Lett. 1982, 23, 409-412; (d) Hosomi, A.; Sakata, Y.; Sakurai, H. Tetrahedron Lett. 1984, 25, 2383-2386; (e) Brown, D. S.; Bruno, M.; Davenport, R.; Ley, S. V. Tetrahedron 1989, 45, 4293-4308.
21. (a) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon: New York, 1983; pp. 209-221. For examples of these reactions, see: (b) Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976-4978; (c) Schmidt, R. R.; Hoffmann, M. Tetrahedron Lett. 1982, 23, 409-412; (d) Hosomi, A.; Sakata, Y.; Sakurai, H. Tetrahedron Lett. 1984, 25, 2383-2386; (e) Brown, D. S.; Bruno, M.; Davenport, R.; Ley, S. V. Tetrahedron 1989, 45, 4293-4308.
22. (a) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon: New York, 1983; pp. 209-221. For examples of these reactions, see: (b) Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976-4978; (c) Schmidt, R. R.; Hoffmann, M. Tetrahedron Lett. 1982, 23, 409-412; (d) Hosomi, A.; Sakata, Y.; Sakurai, H. Tetrahedron Lett. 1984, 25, 2383-2386; (e) Brown, D. S.; Bruno, M.; Davenport, R.; Ley, S. V. Tetrahedron 1989, 45, 4293-4308.
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24. See Ref. 9c. For an alternative explanation for this type of stereocontrol, see: Stewart A.O., Williams R.M. J. Am. Chem. Soc. 107:1985;4289-4296.
25. Takada T., Sakurai H., Hirao T. J. Org. Chem. 66:2001;300-302.
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