Intramolecular Heck Reaction of Hex-2-enopyranosides: An Easy Entry to Cis-Fused Furo-or Pyrano[2,3b]pyranones

Synlett

Volumn 1996, Issue 4, 1996, Pages 327-329

  Tenaglia, Alphonse ^a   Karl, François ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002653884     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5402     Document Type: Article

References (32)

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2. b) Overman, L. E.; Abelman, M. M.; Kucera, D. J.; Tran, D. V.; Ricca, D. J. Pure Appl. Chem. 1992, 64, 1813;
3. c) Heumann, A. in "Stereochemistry of Organometallic and Inorganic Compounds", Vol. 5, Elsevier: Amsterdam, 1994, pp 557-623.
4. Overman, L. E. Pure Appl. Chem. 1994, 66, 1423.
5. a) Melpolder, J. B.; Heck, R. F. J. Org. Chem. 1976, 41, 265;
6. b) Chalk, A. J.; Magennis, S. A. J. Org. Chem. 1976, 41, 273 and 1206;
7. c) Kondo, K.; Sodeoka, M.; Mori, M.; Shibasaki, M. Synthesis, 1993, 920 and references cited therein.
8. Tenaglia, A.; Barillé, D. Synlett, 1995, 776.
9. The difficulty to perform the intramolecular Heck reaction with carbohydrate precursors is emphasized. See: Nguefack, J.-F.; Bolitt, V.; Sinou, D. J. Chem. Soc., Chem. Commun. 1995, 1893.
10. Furo[2,3b]pyran: a) Luebbers, T.; Schaefer, H. J. Synlett 1992, 743; b) Mellor, J. M.; Mohammed, S. Tetrahedron 1993, 49, 7557; c) Pandey, G.; Sesha Poleswara Rao, K.S.; Soma Sekhar, B. B. V. J. Chem. Soc., Chem. Commun., 1993, 1636; d) Hackmann, C.; Schaefer, H. J. Tetrahedron 1993, 49, 4559; e) Inokuchi, T.; Kawaguchi, H.; Aoki, K.; Yoshida, A.; Torii, S. Bull. Chem. Soc. Jpn. 1994, 67, 595; f) Lesueur, C.; Nouguier, R.; Bertrand, M. P.; Hoffmann, P.; De Mesmaeker, A. Tetrahedron 1994, 50, 5369 and references cited therein; g) Cossy, J.; Ranaivosata, J.-L; Bellosta, V. Tetrahedron Lett. 1994, 35, 8161; h) Vaupel, A.; Knochel, P. Tetrahedron Lett. 1994, 35, 8349.
11. Furo[2,3b]pyran: a) Luebbers, T.; Schaefer, H. J. Synlett 1992, 743; b) Mellor, J. M.; Mohammed, S. Tetrahedron 1993, 49, 7557; c) Pandey, G.; Sesha Poleswara Rao, K.S.; Soma Sekhar, B. B. V. J. Chem. Soc., Chem. Commun., 1993, 1636; d) Hackmann, C.; Schaefer, H. J. Tetrahedron 1993, 49, 4559; e) Inokuchi, T.; Kawaguchi, H.; Aoki, K.; Yoshida, A.; Torii, S. Bull. Chem. Soc. Jpn. 1994, 67, 595; f) Lesueur, C.; Nouguier, R.; Bertrand, M. P.; Hoffmann, P.; De Mesmaeker, A. Tetrahedron 1994, 50, 5369 and references cited therein; g) Cossy, J.; Ranaivosata, J.-L; Bellosta, V. Tetrahedron Lett. 1994, 35, 8161; h) Vaupel, A.; Knochel, P. Tetrahedron Lett. 1994, 35, 8349.
12. Furo[2,3b]pyran: a) Luebbers, T.; Schaefer, H. J. Synlett 1992, 743; b) Mellor, J. M.; Mohammed, S. Tetrahedron 1993, 49, 7557; c) Pandey, G.; Sesha Poleswara Rao, K.S.; Soma Sekhar, B. B. V. J. Chem. Soc., Chem. Commun., 1993, 1636; d) Hackmann, C.; Schaefer, H. J. Tetrahedron 1993, 49, 4559; e) Inokuchi, T.; Kawaguchi, H.; Aoki, K.; Yoshida, A.; Torii, S. Bull. Chem. Soc. Jpn. 1994, 67, 595; f) Lesueur, C.; Nouguier, R.; Bertrand, M. P.; Hoffmann, P.; De Mesmaeker, A. Tetrahedron 1994, 50, 5369 and references cited therein; g) Cossy, J.; Ranaivosata, J.-L; Bellosta, V. Tetrahedron Lett. 1994, 35, 8161; h) Vaupel, A.; Knochel, P. Tetrahedron Lett. 1994, 35, 8349.
13. Furo[2,3b]pyran: a) Luebbers, T.; Schaefer, H. J. Synlett 1992, 743; b) Mellor, J. M.; Mohammed, S. Tetrahedron 1993, 49, 7557; c) Pandey, G.; Sesha Poleswara Rao, K.S.; Soma Sekhar, B. B. V. J. Chem. Soc., Chem. Commun., 1993, 1636; d) Hackmann, C.; Schaefer, H. J. Tetrahedron 1993, 49, 4559; e) Inokuchi, T.; Kawaguchi, H.; Aoki, K.; Yoshida, A.; Torii, S. Bull. Chem. Soc. Jpn. 1994, 67, 595; f) Lesueur, C.; Nouguier, R.; Bertrand, M. P.; Hoffmann, P.; De Mesmaeker, A. Tetrahedron 1994, 50, 5369 and references cited therein; g) Cossy, J.; Ranaivosata, J.-L; Bellosta, V. Tetrahedron Lett. 1994, 35, 8161; h) Vaupel, A.; Knochel, P. Tetrahedron Lett. 1994, 35, 8349.
14. Furo[2,3b]pyran: a) Luebbers, T.; Schaefer, H. J. Synlett 1992, 743; b) Mellor, J. M.; Mohammed, S. Tetrahedron 1993, 49, 7557; c) Pandey, G.; Sesha Poleswara Rao, K.S.; Soma Sekhar, B. B. V. J. Chem. Soc., Chem. Commun., 1993, 1636; d) Hackmann, C.; Schaefer, H. J. Tetrahedron 1993, 49, 4559; e) Inokuchi, T.; Kawaguchi, H.; Aoki, K.; Yoshida, A.; Torii, S. Bull. Chem. Soc. Jpn. 1994, 67, 595; f) Lesueur, C.; Nouguier, R.; Bertrand, M. P.; Hoffmann, P.; De Mesmaeker, A. Tetrahedron 1994, 50, 5369 and references cited therein; g) Cossy, J.; Ranaivosata, J.-L; Bellosta, V. Tetrahedron Lett. 1994, 35, 8161; h) Vaupel, A.; Knochel, P. Tetrahedron Lett. 1994, 35, 8349.
15. Furo[2,3b]pyran: a) Luebbers, T.; Schaefer, H. J. Synlett 1992, 743; b) Mellor, J. M.; Mohammed, S. Tetrahedron 1993, 49, 7557; c) Pandey, G.; Sesha Poleswara Rao, K.S.; Soma Sekhar, B. B. V. J. Chem. Soc., Chem. Commun., 1993, 1636; d) Hackmann, C.; Schaefer, H. J. Tetrahedron 1993, 49, 4559; e) Inokuchi, T.; Kawaguchi, H.; Aoki, K.; Yoshida, A.; Torii, S. Bull. Chem. Soc. Jpn. 1994, 67, 595; f) Lesueur, C.; Nouguier, R.; Bertrand, M. P.; Hoffmann, P.; De Mesmaeker, A. Tetrahedron 1994, 50, 5369 and references cited therein; g) Cossy, J.; Ranaivosata, J.-L; Bellosta, V. Tetrahedron Lett. 1994, 35, 8161; h) Vaupel, A.; Knochel, P. Tetrahedron Lett. 1994, 35, 8349.
16. Furo[2,3b]pyran: a) Luebbers, T.; Schaefer, H. J. Synlett 1992, 743; b) Mellor, J. M.; Mohammed, S. Tetrahedron 1993, 49, 7557; c) Pandey, G.; Sesha Poleswara Rao, K.S.; Soma Sekhar, B. B. V. J. Chem. Soc., Chem. Commun., 1993, 1636; d) Hackmann, C.; Schaefer, H. J. Tetrahedron 1993, 49, 4559; e) Inokuchi, T.; Kawaguchi, H.; Aoki, K.; Yoshida, A.; Torii, S. Bull. Chem. Soc. Jpn. 1994, 67, 595; f) Lesueur, C.; Nouguier, R.; Bertrand, M. P.; Hoffmann, P.; De Mesmaeker, A. Tetrahedron 1994, 50, 5369 and references cited therein; g) Cossy, J.; Ranaivosata, J.-L; Bellosta, V. Tetrahedron Lett. 1994, 35, 8161; h) Vaupel, A.; Knochel, P. Tetrahedron Lett. 1994, 35, 8349.
17. Furo[2,3b]pyran: a) Luebbers, T.; Schaefer, H. J. Synlett 1992, 743; b) Mellor, J. M.; Mohammed, S. Tetrahedron 1993, 49, 7557; c) Pandey, G.; Sesha Poleswara Rao, K.S.; Soma Sekhar, B. B. V. J. Chem. Soc., Chem. Commun., 1993, 1636; d) Hackmann, C.; Schaefer, H. J. Tetrahedron 1993, 49, 4559; e) Inokuchi, T.; Kawaguchi, H.; Aoki, K.; Yoshida, A.; Torii, S. Bull. Chem. Soc. Jpn. 1994, 67, 595; f) Lesueur, C.; Nouguier, R.; Bertrand, M. P.; Hoffmann, P.; De Mesmaeker, A. Tetrahedron 1994, 50, 5369 and references cited therein; g) Cossy, J.; Ranaivosata, J.-L; Bellosta, V. Tetrahedron Lett. 1994, 35, 8161; h) Vaupel, A.; Knochel, P. Tetrahedron Lett. 1994, 35, 8349.
18. Pyrano[2,3b]pyran: a) Tietze, L. F.; Schneider, C. Synlett, 1992, 755; b) Durand, R.; Geneste, P.; Joffre, J.; Moreau, C. Stud. Surf. Sci. Catal., 1993, 78, 647; c) Panek, J. S.; Sparks M. A. Tetrahedron Lett., 1989, 29, 4517; d) Hoffmann, R. W.; Giesen, V.; Fuest, M. Liebigs Ann. Chem., 1993, 629; e) Booma, C.; Balasubramanian, K. K. Tetrahedron Lett. 1993, 34, 6757.
19. Pyrano[2,3b]pyran: a) Tietze, L. F.; Schneider, C. Synlett, 1992, 755; b) Durand, R.; Geneste, P.; Joffre, J.; Moreau, C. Stud. Surf. Sci. Catal., 1993, 78, 647; c) Panek, J. S.; Sparks M. A. Tetrahedron Lett., 1989, 29, 4517; d) Hoffmann, R. W.; Giesen, V.; Fuest, M. Liebigs Ann. Chem., 1993, 629; e) Booma, C.; Balasubramanian, K. K. Tetrahedron Lett. 1993, 34, 6757.
20. Pyrano[2,3b]pyran: a) Tietze, L. F.; Schneider, C. Synlett, 1992, 755; b) Durand, R.; Geneste, P.; Joffre, J.; Moreau, C. Stud. Surf. Sci. Catal., 1993, 78, 647; c) Panek, J. S.; Sparks M. A. Tetrahedron Lett., 1989, 29, 4517; d) Hoffmann, R. W.; Giesen, V.; Fuest, M. Liebigs Ann. Chem., 1993, 629; e) Booma, C.; Balasubramanian, K. K. Tetrahedron Lett. 1993, 34, 6757.
21. Pyrano[2,3b]pyran: a) Tietze, L. F.; Schneider, C. Synlett, 1992, 755; b) Durand, R.; Geneste, P.; Joffre, J.; Moreau, C. Stud. Surf. Sci. Catal., 1993, 78, 647; c) Panek, J. S.; Sparks M. A. Tetrahedron Lett., 1989, 29, 4517; d) Hoffmann, R. W.; Giesen, V.; Fuest, M. Liebigs Ann. Chem., 1993, 629; e) Booma, C.; Balasubramanian, K. K. Tetrahedron Lett. 1993, 34, 6757.
22. Pyrano[2,3b]pyran: a) Tietze, L. F.; Schneider, C. Synlett, 1992, 755; b) Durand, R.; Geneste, P.; Joffre, J.; Moreau, C. Stud. Surf. Sci. Catal., 1993, 78, 647; c) Panek, J. S.; Sparks M. A. Tetrahedron Lett., 1989, 29, 4517; d) Hoffmann, R. W.; Giesen, V.; Fuest, M. Liebigs Ann. Chem., 1993, 629; e) Booma, C.; Balasubramanian, K. K. Tetrahedron Lett. 1993, 34, 6757.
23. Ferrier, R. J.; Prasad, M. J. Chem. Soc. (C), 1969, 570;
24. b) ref. 7a.
25. Conditions A, B or C (see Table) used even at increased temperature (140°C) left unchanged 2 (or 3d) with precipitation of metallic palladium and >90% recovered starting material.
26. No definitive mechanistic studies on this elementary step based on the generally accepted stereoelectronic necessity for syn Pd β-H elimination are known. Apparent trans β-H elimination have been reported, see: Friestad, G. K.; Branchaud, B.P. Tetrahedron Lett. 1995, 36, 7047 and references cited therein.
27. The lack of syn β-H to perform (a) an anion capture process or (b) an intramolecular Heck-type cross-coupling, in tandem with a Heck-type cyclization has been reported; a) Grigg, R.; Dorrity, M. J.; Malone, J. F.; Sridharan, V.; Sukirthalingham, S. Tetrahedron Lett. 1990, 31, 1343; b) Larock, R. C.; Lee, N. H. Tetrahedron Lett. 1991, 32, 5911.
28. The lack of syn β-H to perform (a) an anion capture process or (b) an intramolecular Heck-type cross-coupling, in tandem with a Heck-type cyclization has been reported; a) Grigg, R.; Dorrity, M. J.; Malone, J. F.; Sridharan, V.; Sukirthalingham, S. Tetrahedron Lett. 1990, 31, 1343; b) Larock, R. C.; Lee, N. H. Tetrahedron Lett. 1991, 32, 5911.
29. 3: C, 71.54; H, 6.47. Found: C, 71.46; H, 6.52.
30. 2OH), Indicates that this hydrogen is axial thereby supporting the stereochemistry depicted as follows with increased stabilization of an axial anomeric C-O bond. The major isomer reveals H-2 (δ 3.38) as a ddd, J = 3.2, 7.1, and 9.7 Hz which supports a slightly distorted chair conformation for the pyranone moiety. (Equation Presented)
31. Karabelas, K.; Hallberg, A. J. Org. Chem 1986, 51, 5286.
32. Control experiments have shown that no epimerization at the anomeric carbon was observed under the reaction conditions for cyclization.