Synthesis of Furo[2,3b]furans and Furo[2,36]pyrans via rhodium-catalyzed tandem hydroformylation/acetalization

Organic Letters

Volumn 4, Issue 2, 2002, Pages 289-291

  Roggenbuck, Rafael ^a   Schmidt, Andreas ^a   Eilbracht, Peter ^a  

^a TU DORTMUND UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALKENE; FURAN DERIVATIVE; PYRAN DERIVATIVE; RHODIUM;

ACETYLATION; ALKYLATION; ARTICLE; CATALYSIS; CHEMISTRY; SYNTHESIS;

ACETYLATION; ALCOHOLS; ALKENES; ALKYLATION; CATALYSIS; FURANS; PYRANS; RHODIUM;

EID: 0037165376     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol017083o     Document Type: Article

References (27)

1. (a) Elliott, M. C. J. Chem. Soc., Perkin Trans. I 1998, 4175.
2. (b) Burns, C. J.; Middleton, D. S. Contemp. Org. Synth. 1996, 3, 229.
3. Van Beek, T. A.; de Groot, A. Reel. Trav. Chim. Pays-Bas 1986, 105, 513.
4. (a) Chen, H.; Tan, R.; Liu, Z. L.; Zhang, Y. J. Nat. Prod. 1996, 59, 668.
5. (b) Kizu, H.; Sugita, N.; Tomimori, T. Chem. Phann. Bull. 1998, 46, 988.
6. (a) Schuda, P. Top. Curr. Chem. 1980, 91, 75.
7. (b) Minto, R. E.; Townsend, C. A. Chem. Rev. 1997, 97, 2537.
8. (a) Busby, W. F., Jr.; Wogan, G. N. In Chemical Carcinogens, 2nd ed.; Searle, C., Ed.; American Chemical Society: Washington, DC, 1984; Vol. 182, pp 945-1136.
9. (b) Wogan, G. N. Bacterial. Rev. 1966, 30, 460.
10. (c) The Toxicology of Aflatoxins; Eaton, D. L., Groopman, J. D., Eds.; Academic Press: San Diego, 1994.
11. (a) Lorenzo, E.; Alonso, F.; Vus, M. Tetrahedron 2000, 56, 1745.
12. (b) Vader, J.; Sengers, H.; de Groot, A. Tetrahedron 1989, 45, 2131.
13. (c) . Gorst-Allman, C. P.; Steyn, P. S. J. Chem. Soc., Perkin Trans, 1 1987, 163.
14. (d) Bando, T.; Shishido, K. Synlett 1997, 665.
15. (a) Eilbracht, P.; Bärfacker, L.; Buss, C.; Hollmann, C.; Kitsos-Rzychon, B. E.; Kranemann, C. L.; Rische, T.; Roggenbuck, R.; Schmidt, A. Chem. Rev. 1999, 99, 3329.
16. (b) Botteghi, C.; Ganzerla, R.; Lenarda, M.; Moretti, G. J. Mol. Catal. 1987, 40, 129.
17. Breit, B.; Seiche, W. Synthesis 2001, 1.
18. de Leon, C. Y.; Ganem, B. Tetrahedron 1997, 53, 7731.
19. 3 in 10 mL of dichloromethane is heated for 20 h at 120 °C in an autoclave under an atmosphere of 45 bar carbon monoxide and 15 bar hydrogen. Purification of the crude product by column chromatography on basic alumina with MTBE followed by ethanol as eluants gives 411 mg (3.6 mmol) of perhydrofuro[2, 3b]furan (2a).
20. Guijarro, A.; Vus, M. Tetrahedron 1994, 50, 13269.
21. (a) Wang, B.; Zhang, H.; Zheng, A.; Wang, W, Bioorg. Med. Chem. 1998, 6, 417.
22. (b) Alberola, A.; Ortega, A. G.; Pedrosa, R.; Bragado, J. L. P.; Amo, J. F. R. J. Heterocycl. Chem. 1983,715.
23. (c) Boyd, D. R.; Sharma, N. D.; Boyle, R.; Evans, T. A.; Malone, J. F.; McCombie, K. M.; Dalton, H.; Chima, J. J. Chem. Soc., Perkin Trans, 1 1996, 1757.
24. Nozaki, K.; Li, W.; Horiuchi, T.; Takaya, H. Tetrahedron Lett. 1997, 38, 2611.
25. Alemán, A.; Donate, P. M.; da Suva, R.; da Suva, G. V. J. J. Org. Chem. 1999, 64, 5712.
26. Eya, B. K.; Otsuka, T.; Kuba, I.; Wood, D. L. Tetrahedron 1990, 46, 2695.
27. Yasuda, H.; Okamoto, T.; Mashima, K. J. Organomet. Chem. 1989, 363, 61.