Preparation of methylfuro[3,4-b] [1,4]benzodioxinones as intermediates for the synthesis of substituted polycyclic systems. Importance of the acid used as catalyst

Tetrahedron

Volumn 55, Issue 40, 1999, Pages 11843-11852

  Bozzo, Consol ^a   Pujol, M Dolors ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Benzodioxins; Lactonization; Polycyclic heterocyclic compounds

Indexed keywords

AMINOKETONE; DIMETHOXANE; LACTONE; METHYLFURO[3,4 B][1,4]BENZODIOXINONE DERIVATIVE; POLYCYCLIC HYDROCARBON; PROPIONIC ACID; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CATALYSIS; CYCLIZATION; DRUG SYNTHESIS; MOLECULAR INTERACTION; PRIORITY JOURNAL; SPAIN; SYNTHESIS;

EID: 0033214435     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00670-5     Document Type: Article

References (22)

1. a) Cooke, M.P., Jr. J. Org. Chem. 1986, 51, 951.
2. b) Fukuyama, Y.; Kirkemo, C.L.; White, J.D. J. Am. Chem. Soc. 1977, 99, 646.
3. c) Nicolaou, K.C.; Daines, R.A.; Chakraborty, T.K. J. Am. Chem. Soc. 1987, 709, 2208.
4. d) Jong, J.C.; Bolhuis, F.; Feringa, B.L. Tetrahedron: Asymm. 1991, 2, 1247.
5. a) Jung, M.E.; Lowen, G.T. Tetrahedron Lett. 1986, 27, 5319.
6. b) Keller-Juslén, C.; Kuhn, M.; von Wartburg, A. J. Med. Chem. 1971, 14, 936.
7. a) Pelter, A.; Ward, R.S.; Jones, D.M.; Moddocks, P.J. J. Chem. Soc. Perkin. Trans. 1 1993, 2621.
8. b) Middel, O.; Woerdenbarg, J.; Uden, W.; Oeveren, A.; Jansen, J.F.G.A.; Feringa, B.; Konings, W.T.; Pras, N.; Kellog, R.M. J. Med. Chem. 1995, 38, 2112.
9. a) Iwasaki, T.; Kondo, K.; Kurada, T.; Moritani, Y.; Yamagata, S.; Sugiura, M.; Kikkawa, H.; Kaminuma, O.; Ikezawa, K. J. Med. Chem. 1996, 39, 2696.
10. a) Park, P.; Broka, C.A.; Johnson, B.F.; Kishi, Y. J. Am. Chem. Soc. 1987, 109, 6205.
11. b) Fuji, K.; Node, M.; Terada, S.; Murata, M.; Nagasawa, H.; Taga, T.; Machida, K. J. Am. Chem. Soc. 1985, 707, 6404.
12. c) Fuji, K.; Node, M.; Murata, M.; Terada, S.; Hashimoto, K. Tetrahedron Lett. 1986, 27, 5381.
13. a) Kimura, Y.; Regen, S.L. J. Org. Chem. 1983, 48, 1533.
14. b) Galli, C.; Mandolini, L. Org. Synth. 1978, 58, 98.
15. Ansell, M.F.; Palmer, M.H. Q. Rev. Chem. Soc. 1964, 18, 211.
16. Guillaumet, G.; Coudert, G.; Loubinoux, B. Tetrahedron Lett. 1979, 45, 4379.
17. Sucrow, W.; Klein, U. Chem. Ber. 1975, 108, 48.
18. a) Puterbaugh, W.K.; Hauser, C.R. J. Org. Chem. 1964, 29, 853.
19. b) Comins, D.L.; Brown, J.D. J. Org. Chem. 1986, 51, 3566.
20. Koo, J; Avarian, S.; Martin, G.J. J. Am. Chem. Soc. 1955, 77, 5373.
21. Ruiz, N.; Buon, C.; Pujol, M.D.; Guillaumet, G.; Coudert, G. Synth.Commun. 1996, 26, 2057.
22. Guillaumet, G.; Coudert, G.; Thiery, V.; Adam, G.; Bizot-Espiard, J.-G.; Pfeiffer, B.; Renard, P. EP 624.582 A1, 1994.