The regiospecific C-3 lithiation of 5-ethyl-2-furoic acid: An approach to key natural product intermediates

Applied Organometallic Chemistry

Volumn 10, Issue 5, 1996, Pages 389-392

  Perry, Philip J ^a   Pavlidis, Vasilios H ^a   Naik, Manisha ^a  

^a DE MONTFORT UNIVERSITY   (United Kingdom)

Author keywords

2 furoic acid; 5 ethyl 2 furoic acid; Butyl lithium; Furonaphthoquinone; Lithium di isopropylamide (LDA); Regiospecific lithiation

Indexed keywords

EID: 0000262978     PISSN: 02682605     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0739(199606)10:5<389::AID-AOC488>3.0.CO;2-J     Document Type: Article

References (14)

1. D. W. Knight and A. P. Nott, J. Chem. Soc. Perkin Trans. 1 1125 (1981).
2. D. W. Slocum and C. A. Jennings, J. Org. Chem. 41, 3653 (1976); P. Beak and R. A. Brown, J. Org. Chem. 47, 34 (1982); V. Snieckus, Chem. Rev. 90, 879 (1990), and references therein.
3. D. W. Slocum and C. A. Jennings, J. Org. Chem. 41, 3653 (1976); P. Beak and R. A. Brown, J. Org. Chem. 47, 34 (1982); V. Snieckus, Chem. Rev. 90, 879 (1990), and references therein.
4. D. W. Slocum and C. A. Jennings, J. Org. Chem. 41, 3653 (1976); P. Beak and R. A. Brown, J. Org. Chem. 47, 34 (1982); V. Snieckus, Chem. Rev. 90, 879 (1990), and references therein.
5. V. H. Pavlidis and P. J. Perry, BP Appl. 9419235.8/1994.
6. P. J. Perry, V. H. Pavlidis, J. A. Hadfield and I. G. C. Coutts, J. Chem. Soc., Perkin Trans. 1 1085 (1995).
7. C. C. Lopes, R. S. C. Lopes, A. V. Pinto and P. R. R. Costa, J. Heterocyclic Chem. 21, 621 (1984); C. L Zani, A. B. de Oliveria and V. Snieckus, Tetrahedron Lett. 28, 6561 (1987); C. C. Lopes, E. L. S. Lima, A. J. Monteiro and P. R. R. Costa, Synth. Commun. 18, 1731 (1988).
8. C. C. Lopes, R. S. C. Lopes, A. V. Pinto and P. R. R. Costa, J. Heterocyclic Chem. 21, 621 (1984); C. L Zani, A. B. de Oliveria and V. Snieckus, Tetrahedron Lett. 28, 6561 (1987); C. C. Lopes, E. L. S. Lima, A. J. Monteiro and P. R. R. Costa, Synth. Commun. 18, 1731 (1988).
9. C. C. Lopes, R. S. C. Lopes, A. V. Pinto and P. R. R. Costa, J. Heterocyclic Chem. 21, 621 (1984); C. L Zani, A. B. de Oliveria and V. Snieckus, Tetrahedron Lett. 28, 6561 (1987); C. C. Lopes, E. L. S. Lima, A. J. Monteiro and P. R. R. Costa, Synth. Commun. 18, 1731 (1988).
10. R. H. Thomson, Naturally Occurring Quinones, 2nd edn, Academic Press, London, 1971, p. 220.
11. T. Sakai, K. Miyata, S. Tsuboi, A. Takeda, M. Utaka and S. Torii, Bull. Chem. Soc. Jpn. 62, 3537 (1989).
12. A. J. Carpenter and D. J. Chadwick, Tetrahedron Lett. 26, 1777 (1985).
13. S. Yu and B. A. Keay, J. Chem. Soc., Perkin Trans. 1 2600 (1991).
14. T. Masamune, M. Ono and H. Matsue, Bull. Chem. Soc. Jpn. 48, 491 (1975).