Pyridoxal-mediated cycloaromatization of an enediyne model system

Tetrahedron Letters

Volumn 37, Issue 30, 1996, Pages 5397-5400

  Wakayama, Masakazu ^a   Nemoto, Hisao ^a   Shibuya, Masayuki ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BIPHENYL DERIVATIVE; ISOCHROMAN DERIVATIVE;

AROMATIZATION; ARTICLE; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030598009     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01087-8     Document Type: Article

References (23)

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13. 10. S-trans isomer of 6 (3 % yield) was obtained as a by-product.
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17. 13. For an alternative experiment for Scheme 4, the reaction was carried out in the presence of 40 equiv of cyclohexadiene to give 8 in a higher yield (26 %), while product 9 was not detected from the products, indicating the radical mechanism is preferable for these reactions.
18. 14. Several examples of homolytic intramolecular 1,5-hydrogen atom shift have been reported in the field of enediyne chemistry. See, Chin, D.-H.; Goldberg, I. H. J. Am. Chem. Soc. 1992, 114, 1914-1915; Wender, P. A.; Tebbe, M. J. Tetrahedron, 1994, 50, 1419-1934; Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Riche, C.; Chiaroni, A.; Grierson, D. S. Tetrahedron 1994, 50, 1469-1502; Kawata, S.; Oishi, T.; Hirama, M. Tetrahedron Lett. 1994, 35, 4595-4598; Wang, Z.; Wang, K. K. J. Org. Chem. 1994, 59, 4738-4742.
19. 14. Several examples of homolytic intramolecular 1,5-hydrogen atom shift have been reported in the field of enediyne chemistry. See, Chin, D.-H.; Goldberg, I. H. J. Am. Chem. Soc. 1992, 114, 1914-1915; Wender, P. A.; Tebbe, M. J. Tetrahedron, 1994, 50, 1419-1934; Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Riche, C.; Chiaroni, A.; Grierson, D. S. Tetrahedron 1994, 50, 1469-1502; Kawata, S.; Oishi, T.; Hirama, M. Tetrahedron Lett. 1994, 35, 4595-4598; Wang, Z.; Wang, K. K. J. Org. Chem. 1994, 59, 4738-4742.
20. 14. Several examples of homolytic intramolecular 1,5-hydrogen atom shift have been reported in the field of enediyne chemistry. See, Chin, D.-H.; Goldberg, I. H. J. Am. Chem. Soc. 1992, 114, 1914-1915; Wender, P. A.; Tebbe, M. J. Tetrahedron, 1994, 50, 1419-1934; Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Riche, C.; Chiaroni, A.; Grierson, D. S. Tetrahedron 1994, 50, 1469-1502; Kawata, S.; Oishi, T.; Hirama, M. Tetrahedron Lett. 1994, 35, 4595-4598; Wang, Z.; Wang, K. K. J. Org. Chem. 1994, 59, 4738-4742.
21. 14. Several examples of homolytic intramolecular 1,5-hydrogen atom shift have been reported in the field of enediyne chemistry. See, Chin, D.-H.; Goldberg, I. H. J. Am. Chem. Soc. 1992, 114, 1914-1915; Wender, P. A.; Tebbe, M. J. Tetrahedron, 1994, 50, 1419-1934; Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Riche, C.; Chiaroni, A.; Grierson, D. S. Tetrahedron 1994, 50, 1469-1502; Kawata, S.; Oishi, T.; Hirama, M. Tetrahedron Lett. 1994, 35, 4595-4598; Wang, Z.; Wang, K. K. J. Org. Chem. 1994, 59, 4738-4742.
22. 14. Several examples of homolytic intramolecular 1,5-hydrogen atom shift have been reported in the field of enediyne chemistry. See, Chin, D.-H.; Goldberg, I. H. J. Am. Chem. Soc. 1992, 114, 1914-1915; Wender, P. A.; Tebbe, M. J. Tetrahedron, 1994, 50, 1419-1934; Audrain, H.; Skrydstrup, T.; Ulibarri, G.; Riche, C.; Chiaroni, A.; Grierson, D. S. Tetrahedron 1994, 50, 1469-1502; Kawata, S.; Oishi, T.; Hirama, M. Tetrahedron Lett. 1994, 35, 4595-4598; Wang, Z.; Wang, K. K. J. Org. Chem. 1994, 59, 4738-4742.
23. 2: 267.1259. Found: 267.1277.