6-Endo- and 5-exo-digonal cyclizations of o-hydroxyphenyl ethynyl ketones: A key step for highly selective benzopyranone formation

Tetrahedron

Volumn 52, Issue 28, 1996, Pages 9427-9446

  Nakatani, Kazuhiko ^a   Okamoto, Akimitsu ^a   Saito, Isao ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOFURAZAN DERIVATIVE; HEDAMYCIN; KAPURIMYCIN A1; KETONE; PLURAMYCIN;

ARTICLE; COMPETITIVE INHIBITION; COVALENT BOND; CYCLIZATION; DNA STRUCTURE; DNA SYNTHESIS; NONHUMAN; PRIORITY JOURNAL; PROTON TRANSPORT; REACTION ANALYSIS;

EID: 0030575380     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00480-2     Document Type: Article

References (34)

1. 1. (a) Hara, M.; Mokudai, T.; Kobayashi, E.; Gomi, K.; Nakano, H. J. Antibiot. 1990, 43, 1513-1518.
2. (b) Yoshida, M.; Hara, M.; Saitoh, Y.; Sano, H. J. Antibiot. 1990, 43, 1519-1523.
3. 2. For a review of the antibiotics of the pluramycin group, see: Séquin, U. Fortschr. Chem. Naturst. 1986, 50, 57-122.
4. 3. (a) Kondo, S.; Miyamoto, M.; Naganawa, H.; Takeuchi, T.; Umezawa, H. J. Antibiot. 1977, 30, 1143-1145.
5. (b) Maeda, K.; Takeuchi, T.; Nitta, K.; Yagishita, K.; Utahara, R.; Osato, T.; Ueda, M.; Kondo, S.; Okami, Y.; Umesawa, H. J. Antibiot., Ser. A 1956, 9, 75-81.
6. 4. (a) Séquin, U.; Bedford, C. T.; Chung, S. K.; Scott, A. I. Helv. Chim. Acta 1977, 60, 896-906.
7. (b) Zehnder, M.; Séquin, U.; Nadig, H. Helv. Chim. Acta 1979, 62, 2525-2533.
8. 5. Bennet, G. N. Nucleic Acids Res. 1982, 10, 4581-4594.
9. 6. Hara, M.; Yoshida, M.; Nakano, H. Biochemistry, 1990, 29, 10449-10455.
10. 7. Chan, K.L.; Sugiyama, H.; Saito, I. Tetrahedron Lett. 1991, 52, 7719-7722.
11. 8. Hansen, M.; Hurley, L. J. Am. Chem. Soc. 1995, 117, 2421-2429.
12. 9. (a) Hauser, F. M.; Rhee, R. P. J. Am. Chem. Soc. 1979, 101, 1628-1629.
13. (b) Hauser, F. M.; Rhee, R. P. J. Org. Chem. 1980, 45, 3061-3068.
14. 10. For other synthetic studies for pluramycin antibiotics, see: (a) Parker, K. A.; Koh, Y.-H. J. Am. Chem. Soc. 1994, 116, 11149-11150.
15. (b) Dubois, E.; Beau, J.-M. J. Chem. Soc., Chem. Commun. 1990, 1191-1192.
16. (c) Dubois, E.; Beau, J.-M. Carbohydr. Res. 1992, 228, 103-120.
17. 11. Hirao, I.; Yamaguchi, M.; Hamada, M. Synthesis 1984, 1076-1078.
18. 12. For a general synthesis of 4H-chromen-4-ones, see: Hepworth, J.D. Pyrans and Fused Pyrans: (iii) Synthesis and Application in Comprehensive Heterocyclic Chemistry, Katritzky, A.R., Rees, C.W. Ed.; Vol. 3, Pergamon Press, Oxford, 1984, pp 737-883.
19. 13. (a) Baldwin, J. K. J. Chem. Soc., Chem. Commun. 1976, 734-736.
20. (b) Baldwin, J. K.; Cutting, J.; Dupont, W.; Kruse, L.; Silberman, L.; Thomas, R. C. J. Chem. Soc., Chem. Commun. 1976, 736-738.
21. 14. Garcia H.; Iborra, S.; Primo, J.; Miranda, M.A. J. Org. Chem. 1986, 51, 4432-4436.
22. 15. For recent studies of a 6-endo-digonal addition to an unactivated carbon-carbon triple bond, see: Padwa, A.; Krumpe, K. K.; Weingaten, M. D. J. Org. Chem. 1995, 60, 5595-5603.
23. 16. For a related approach involving Pd-catalyzed carbonylation of o-iodophenol with terminal alkynes giving chromenoes, see Torii, S.; Okumoto, H.; Sadakane, M.; Shostakovsky, M.V.; Ponomaryov, A.B.; Kalinin, V.N. Tetrahedron 1993, 31, 6773-6784.
24. 17. A preliminary account describing portions of this work has been published. Nakatani, K.; Okamoto, A.; Yamanuki, M.; Saito, I. J. Org. Chem. 1994, 59, 4360-4361.
25. 18. All semiempilical and ab initio calculations were carried out using Spartan molecular modeling software (version 3.1).
26. 19. For related ab initio studies of the nucleophilic addition to the acetylenic bonds, see: (a) Eisenstein, O.; Procter, G.; Dunitz, J. D. Helv. Chim. Acta 1978, 61, 2538-2541.
27. (b) Dykstra, C. E.; Arduengo, A. J.; Fukunaga, T. J. Am. Soc. Chem. 1978, 100, 6007-6012.
28. (c) Strozier, R. W.; Caramella, P.; Houk, K. N. J. Am. Soc. Chem. 1979, 101, 1340-1343.
29. (d) Houk, K. N.; Strozeiner, R. W.; Rozeboom, M. D.; Nagase, S. J. Am. Soc. Chem. 1982, 104, 323-325.
30. 20. The energy gap between the two conformers calculated at the 3-21G(*) level became large (4.72 kcal/mol), with the s-trans conformer being more stable.
31. 21. For examples of syn addition, see: Bailey, W. F.; Ovaska, T. V. J. Am. Chem. Soc. 1993, 115, 3080-3090 and references cited therein.
32. 22. Analyses of the vibrational frequencies were carried out using Gaussian 92 program. Frisch, M. J.; Trucks, G. W.; Head-Gordon, M.; Gill, P. M. W.; Wong, M. W.; Foresman, J. B.; Johnson, B. G.; Schlegel, H. B.; Robb, M. A.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A. Gaussian, Inc. Pittsburgh PA, 1992.
33. 23. The interconversion was observed for chalcogenachromanones upon the direct lithiation at the C2 position. Detty, M. Y.; McGarry, L. W. J. Org. Chem. 1988, 53, 1203-1207.
34. 24. Payard, M.; Couquelet, J. Synthesis, 1979, 889.