Highly diastereoselective and asymmetric Diels-Alder reactions of masked o-benzoquinones with chiral racemic and homochiral furans. Synthesis of optically active tricyclic γ-lactones

Organic Letters

Volumn 5, Issue 10, 2003, Pages 1637-1640

  Chou, Yu Yu ^a   Peddinti, Rama Krishna ^a   Liao, Chun Chen ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

FURAN DERIVATIVE; GAMMA LACTONE DERIVATIVE; QUINONE DERIVATIVE;

ADDITION REACTION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHIRALITY; CYCLOADDITION; DIASTEREOISOMER; DIELS ALDER REACTION; OPTICS; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0141571323     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034278i     Document Type: Article

References (28)

1. (a) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon: Oxford, 1990.
2. (b) Fringuelli, F.; Taticchi, A. Dienes in the Diels-Alder Reaction; Wiley: New York, 1990.
3. (c) Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. E. Angew. Chem., Int. Ed. 2002, 41, 1668-1698.
4. For stoichiometric processes, see: (a) Jurczak, J.; Bauer, T.; Chapuis, C. In Stereoselective Synthesis, 4th ed.; Houben-Weyl; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Ed.; Verlag: Stuttgart, 1995; Vol. E21c, pp 2735-2871.(b) Rück-Braun, K.; Kunz, H. Chiral Auxiliaries in Cycloadditions; Wiley-VCH: New York, 1999; pp 30-71. (c) Enders, D.; Meyer, O. Liebigs Ann. 1996, 1023-1035. (d) Barluenga, J.; Suárez-Sobrino, A.; López, L. A. Aldrichim. Acta 1999, 32, 4-15.
5. For stoichiometric processes, see: (a) Jurczak, J.; Bauer, T.; Chapuis, C. In Stereoselective Synthesis, 4th ed.; Houben-Weyl; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Ed.; Verlag: Stuttgart, 1995; Vol. E21c, pp 2735-2871.(b) Rück-Braun, K.; Kunz, H. Chiral Auxiliaries in Cycloadditions; Wiley-VCH: New York, 1999; pp 30-71. (c) Enders, D.; Meyer, O. Liebigs Ann. 1996, 1023-1035. (d) Barluenga, J.; Suárez-Sobrino, A.; López, L. A. Aldrichim. Acta 1999, 32, 4-15.
6. For stoichiometric processes, see: (a) Jurczak, J.; Bauer, T.; Chapuis, C. In Stereoselective Synthesis, 4th ed.; Houben-Weyl; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Ed.; Verlag: Stuttgart, 1995; Vol. E21c, pp 2735-2871.(b) Rück-Braun, K.; Kunz, H. Chiral Auxiliaries in Cycloadditions; Wiley-VCH: New York, 1999; pp 30-71. (c) Enders, D.; Meyer, O. Liebigs Ann. 1996, 1023-1035. (d) Barluenga, J.; Suárez-Sobrino, A.; López, L. A. Aldrichim. Acta 1999, 32, 4-15.
7. For stoichiometric processes, see: (a) Jurczak, J.; Bauer, T.; Chapuis, C. In Stereoselective Synthesis, 4th ed.; Houben-Weyl; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Ed.; Verlag: Stuttgart, 1995; Vol. E21c, pp 2735-2871.(b) Rück-Braun, K.; Kunz, H. Chiral Auxiliaries in Cycloadditions; Wiley-VCH: New York, 1999; pp 30-71. (c) Enders, D.; Meyer, O. Liebigs Ann. 1996, 1023-1035. (d) Barluenga, J.; Suárez-Sobrino, A.; López, L. A. Aldrichim. Acta 1999, 32, 4-15.
8. For catalytic processes, see: (a) Dias, L. C. J. Braz. Chem. Soc. 1997, 8, 289-332. (b) Evans, D. A.; Johnson, J. S. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York, 1999; Vol. III, pp 1177-1235. (c) Hayashi, Y. In Cycloaddition Reactions in Organic Synthesis; Kobayashi, S., Jorgensen, K. A., Ed.; Wiley-VCH: Weiheim, 2001, pp 5-56. (d) Corey, E. J. Angew. Chem., Int. Ed. 2002, 41, 1650-1667 and also see ref 1c.
9. For catalytic processes, see: (a) Dias, L. C. J. Braz. Chem. Soc. 1997, 8, 289-332. (b) Evans, D. A.; Johnson, J. S. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York, 1999; Vol. III, pp 1177-1235. (c) Hayashi, Y. In Cycloaddition Reactions in Organic Synthesis; Kobayashi, S., Jorgensen, K. A., Ed.; Wiley-VCH: Weiheim, 2001, pp 5-56. (d) Corey, E. J. Angew. Chem., Int. Ed. 2002, 41, 1650-1667 and also see ref 1c.
10. For catalytic processes, see: (a) Dias, L. C. J. Braz. Chem. Soc. 1997, 8, 289-332. (b) Evans, D. A.; Johnson, J. S. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York, 1999; Vol. III, pp 1177-1235. (c) Hayashi, Y. In Cycloaddition Reactions in Organic Synthesis; Kobayashi, S., Jorgensen, K. A., Ed.; Wiley-VCH: Weiheim, 2001, pp 5-56. (d) Corey, E. J. Angew. Chem., Int. Ed. 2002, 41, 1650-1667 and also see ref 1c.
11. For catalytic processes, see: (a) Dias, L. C. J. Braz. Chem. Soc. 1997, 8, 289-332. (b) Evans, D. A.; Johnson, J. S. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York, 1999; Vol. III, pp 1177-1235. (c) Hayashi, Y. In Cycloaddition Reactions in Organic Synthesis; Kobayashi, S., Jorgensen, K. A., Ed.; Wiley-VCH: Weiheim, 2001, pp 5-56. (d) Corey, E. J. Angew. Chem., Int. Ed. 2002, 41, 1650-1667 and also see ref 1c.
12. Liao, C.-C.; Peddinti, R. K. Acc. Chem. Res. 2002, 35, 856-866.
13. For synthetic applications of MOBs, see cited references in 4 and: (a) Feldman, K. S.; Ensel, S. M. J. Am. Chem. Soc. 1994, 116, 3357-3366. (b) Coleman, R. S.; Grant, E. B. J. Am. Chem. Soc. 1995, 117, 10889-10890. (c) Yen, C.-F.; Liao, C.-C. Angew. Chem., Int. Ed. 2002, 41, 4090-4093.
14. For synthetic applications of MOBs, see cited references in 4 and: (a) Feldman, K. S.; Ensel, S. M. J. Am. Chem. Soc. 1994, 116, 3357-3366. (b) Coleman, R. S.; Grant, E. B. J. Am. Chem. Soc. 1995, 117, 10889-10890. (c) Yen, C.-F.; Liao, C.-C. Angew. Chem., Int. Ed. 2002, 41, 4090-4093.
15. For synthetic applications of MOBs, see cited references in 4 and: (a) Feldman, K. S.; Ensel, S. M. J. Am. Chem. Soc. 1994, 116, 3357-3366. (b) Coleman, R. S.; Grant, E. B. J. Am. Chem. Soc. 1995, 117, 10889-10890. (c) Yen, C.-F.; Liao, C.-C. Angew. Chem., Int. Ed. 2002, 41, 4090-4093.
16. For diastereoselective intramolecular Diels-Alder reactions of MOBs, see: Chen, Y.-K.; Peddinti, R. K.; Liao, C.-C. Chem. Commun. 2001, 1340-1341.
17. (a) Chen, C.-H.; Rao, P. D.; Liao, C.-C. J. Am. Chem. Soc. 1998, 120, 13254-13255.
18. (b) Rao, P. D.; Chen, C.-H.; Liao, C.-C. Chem. Commun. 1999, 713-714.
19. For natural products bearing butyrolactone moiety which exhibit interesting and useful biological activities, see: Pettit, G. R.; Grag, G. M.; Ode, R. H. Biosynthetic Products for Cancer Theraphy; Plenum: New York, 1977-1979; Vols. I-III.
20. 9b were synthesized according to literature procedures. (a) West, F. G.; Gunawardena, U. J. Org. Chem. 1993, 58, 2402-2406. (b) Lee, G. C. M.; Syage, E. T.; Harcourt, D. A.; Holmes, J. M.; Garst, M. E. J. Org. Chem. 1991, 56, 7007-7014. (c) Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1991, 113, 224-232.
21. 9b were synthesized according to literature procedures. (a) West, F. G.; Gunawardena, U. J. Org. Chem. 1993, 58, 2402-2406. (b) Lee, G. C. M.; Syage, E. T.; Harcourt, D. A.; Holmes, J. M.; Garst, M. E. J. Org. Chem. 1991, 56, 7007-7014. (c) Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1991, 113, 224-232.
22. 9b were synthesized according to literature procedures. (a) West, F. G.; Gunawardena, U. J. Org. Chem. 1993, 58, 2402-2406. (b) Lee, G. C. M.; Syage, E. T.; Harcourt, D. A.; Holmes, J. M.; Garst, M. E. J. Org. Chem. 1991, 56, 7007-7014. (c) Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1991, 113, 224-232.
23. Method A. In a representative procedure, to a mixture of a 2-methoxyphenol 7 (0.5 mmol) and a furan derivative (1-6, 1.5 mmol) in MeOH (3 mL) was added DAIB (0.75 mmol) in MeOH (2 mL) during 1 h under stirring at room temperature. After 10 min of stirring, MeOH was removed under reduced pressure and the adducts were separated by silica gel column chromatography.
24. 4 and concentrated under reduced pressure. Thus obtained crude MOB 8 was taken in MeOH (3 mL), to this was added a furan derivative (3 or 4, 1.5 mmol) in MeOH (3 mL), and the resulting mixture stirred at the appropriate temperature (see Tables 1 and 2). After completion of the reaction (see Tables 1 and 2 for reaction time), MeOH was removed under reduced pressure and the adducts were separated by silica gel (neutralized with triethylamine) column chromatography.
25. 12b were synthesized according to literature procedures: (a) Kusakabe, M.; Kitano, Y.; Kobayashi, Y.; Sato, F. J. Org. Chem. 1989, 54, 2085-2091. (b) Dinesh, C. U.; Kumar, P.; Reddy, R. S.; Pandey, B.; Puranik, V. G. Tetrahedron: Asymmetry 1995, 6, 2961-2970.
26. 12b were synthesized according to literature procedures: (a) Kusakabe, M.; Kitano, Y.; Kobayashi, Y.; Sato, F. J. Org. Chem. 1989, 54, 2085-2091. (b) Dinesh, C. U.; Kumar, P.; Reddy, R. S.; Pandey, B.; Puranik, V. G. Tetrahedron: Asymmetry 1995, 6, 2961-2970.
27. (a) (+)-11a: CCDC 199010. (b) (+)-11d: CCDC 199012. (c) (±)-13a: CCDC 199011.
28. Domingo, L. R.; Aurell, M. J. J. Org. Chem. 2002, 67, 959-965.