4-endo-Hydroxy-2-oxabicyclo[3.3.0]oct-7-en-3-one as a useful building block in the formal total syntheses of furofurandione natural products

Tetrahedron Letters

Volumn 48, Issue 49, 2007, Pages 8611-8614

  Hon, Yung Son ^a   Chen, Hsien Fan ^a  

^a NATIONAL CHUNG CHENG UNIVERSITY   (Taiwan)

Author keywords

4 endo Hydroxy 2 oxabicyclo 3.3.0 oct 7 en 3 one; 4 epi Ethisolide; Avenaciolide; Ethisolide; Furofurandione; Isoavenaciolide

Indexed keywords

4 ENDO HYDROXY 2 OXABICYCLO[3.3.0]OCT 7 EN 3 ONE; ALKANONE; ALKENYL GROUP; FUROFURANDIONE; HYDROXYL GROUP; LACTONE DERIVATIVE; NATURAL PRODUCT; NITROFURANTOIN; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; EPIMERIZATION; FUNGUS GROWTH; HYDROGENATION; NUCLEAR MAGNETIC RESONANCE; OZONOLYSIS; ROOM TEMPERATURE; SYNTHESIS;

EID: 35748929411     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.10.036     Document Type: Article

References (34)

1. Brookes D., Tidd B.K., and Turner W.B. J. Chem. Soc. (1963) 5385
2. Brookes D., Sternhell S., Tidd B.K., and Turner W.B. Aust. J. Chem. 18 (1965) 373
3. Krohn K., Ludewig K., Aust H.J., Draeger S., and Schutz B. J. Antibiot. 47 (1994) 113
4. Aldridge D.C., and Turner W.B. J. Chem. Soc. (C) (1971) 2431
5. Type A natural product synthesis: For a review of the synthesis of avenaciolide, see:. Martin V.S., Rodriguez C.M., and Martin T. Org. Prep. Proc. Int. 30 (1998) 291
6. for more recent publication, see:. Aggarwal V.K., Davies P.W., and Schmidt A.T. Chem. Commun. (2004) 1232 and references cited therein
7. For the synthesis of avenaciolide and 4-epi-ethisolide, see:. Tsuboi S., Sakamoto J.I., Yamashita H., Sakai T., and Utaka M. J. Org. Chem. 63 (1998) 1102 and references cited therein
8. For the synthesis of 4-epi-ethisolide, see:. Sharma G.V.M., and Krishnudu K. Tetrahedron Lett. 36 (1995) 2661 and references cited therein
9. Type B natural product synthesis: (a) For the syntheses of isoavenaciolide and ethisolide, see:. Wee A.G.H. Tetrahedron 46 (1990) 5065 and references therein
10. Chida N., Tobe T., Suwama M., Ohtsuka M., and Ogawa S. J. Chem. Soc., Perkin Trans. 1 (1992) 2667
11. For the synthesis of isoavenaciolide, see:. McDonald C.E., and Dugger R.W. Tetrahedron Lett. 29 (1988) 2413 and references cited therein
12. For the synthesis of ethisolide, see:. Cossy J., Ranaivosata J.L., and Bellosta V. Tetrahedron Lett. 35 (1994) 1205 and references cited therein
13. For the synthesis of discosiolide, see:. Sharma G.V.M., and Krishnudu K. Tetrahedron: Asymmetry 10 (1999) 869 and references cited therein
14. For the synthesis of avenaciolide and isoavenaciolide, see:. Alcazar E., Kassou M., Matheu I., and Castillon S. Eur. J. Org. Chem. (2000) 2285
15. Udding J.H., Tuijp K.J.M., van Zanden M.N.A., Hiemstra H., and Speckamp W.N. J. Org. Chem. 59 (1994) 1993
16. Burke S.D., Jung K.W., and Perri R.E. Tetrahedron Lett. 35 (1994) 5841
17. Rodriguez C.M., Martin T., and Martin V.S. J. Org. Chem. 61 (1996) 8448
18. Burke S.D., Pacofsky G.J., and Piscopio A.D. J. Org. Chem. 57 (1992) 2228
19. Suzuki K., Miyazawa M., Shimazaki M., and Tsuchihashi G. Tetrahedron Lett. 27 (1986) 6237
20. Narkunan K., and Liu R.S. Chem. Commun. (1998) 1521
21. Parker W.L., and Johnson F. J. Org. Chem. 38 (1973) 2489
22. Parker W.L., and Johnson F. J. Am. Chem. Soc. 91 (1969) 7208
23. Hon Y.S., Hsieh C.H., and Liu Y.W. Tetrahedron 61 (2005) 2713
24. Hon Y.S., and Hsieh C.H. Tetrahedron 62 (2006) 9713
25. Hon Y.S., Hsieh C.H., and Chen H.F. Synth. Commun. 37 (2007) 1635
26. Hon Y.S., Chang F.J., and Lu L. Chem. Commun. (1994) 2041
27. Hon Y.S., and Lin W.C. Tetrahedron Lett. 36 (1995) 7693
28. Hon Y.S., Chang F.J., Lu L., and Lin W.C. Tetrahedron 54 (1998) 5233
29. Hon Y.S., Hsu T.R., Chen C.Y., Lin Y.H., Chang F.R., Hsieh C.H., and Szu P.H. Tetrahedron 59 (2003) 1509
30. Hon Y.S., Liu Y.W., and Hsieh C.H. Tetrahedron 60 (2004) 4837
31. MacKeith R.A., McCague R., Olivo H.F., Roberts S.M., Taylor S.J.C., and Xiong H. Bioorg. Med. Chem. 2 (1994) 387
32. Lubineau A., Auge J., and Lubin N. Tetrahedron Lett. 32 (1991) 7529
33. Bellina F., Biagetti A., Carpita A., and Rossi R. Tetrahedron 57 (2001) 2857
34. Chinchilla R., and Nájera C. Chem. Rev. 107 (2007) 874