Synthesis of (±)-recifeiolide and its homologs via acetylenic lactones

Synthetic Communications

Volumn 26, Issue 20, 1996, Pages 3809-3819

  Mahajan, Jaswant Rai ^a   Resck, Inês Sabioni ^a  

^a UNIVERSITY OF BRASILIA   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

LACTONE DERIVATIVE; MACROLIDE; RECIFEIOLIDE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0029782659     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919608003797     Document Type: Article

References (24)

1. (a) Mahajan, J.R. in "Organic Synthesis in Brazil: An Overview", Comasseto, J.V. and Ferreira, J.T.B. (Eds.). Editoração eletrônica & Multimidia , São Carlos-SP, 1994, pp. 79-87;
2. (b) Mahajan, J.R., Araújo, H.C. and Resck, I.S. J. Braz. Chem. Soc. 1990, 1, 119;
3. (c) Mahajan, J.R. and Silva, C.R. ibid. 1990, 1, 87;
4. (d) Mahajan, J.R., Botelho, J.R. and Resck, I.S. ibid. 1990, 1, 13.
5. For recent reviews see: (a) Rousseau, G. Tetrahedron 1995, 51, 2777; (b) Roxburgh, C.J. ibid. 1993, 49, 10749; (c) Hesse, M., "Ring Elargement in Organic Chemistry", VCH, Weinheim, 1991; (d) Stach, H. and Hesse, M. Tetrahedron 1988, 44, 1573.
6. For recent reviews see: (a) Rousseau, G. Tetrahedron 1995, 51, 2777; (b) Roxburgh, C.J. ibid. 1993, 49, 10749; (c) Hesse, M., "Ring Elargement in Organic Chemistry", VCH, Weinheim, 1991; (d) Stach, H. and Hesse, M. Tetrahedron 1988, 44, 1573.
7. For recent reviews see: (a) Rousseau, G. Tetrahedron 1995, 51, 2777; (b) Roxburgh, C.J. ibid. 1993, 49, 10749; (c) Hesse, M., "Ring Elargement in Organic Chemistry", VCH, Weinheim, 1991; (d) Stach, H. and Hesse, M. Tetrahedron 1988, 44, 1573.
8. For recent reviews see: (a) Rousseau, G. Tetrahedron 1995, 51, 2777; (b) Roxburgh, C.J. ibid. 1993, 49, 10749; (c) Hesse, M., "Ring Elargement in Organic Chemistry", VCH, Weinheim, 1991; (d) Stach, H. and Hesse, M. Tetrahedron 1988, 44, 1573.
9. Mahajan, J.R. and Resck, I.S. J.Chem. Soc., Chem. Commun. 1993, 1748.
10. Resck, I.S. and Mahajan, J.R., 17th Annual Meeting of SBQ, 1994; Abstract QO-042.
11. Moore, B.P. and Brown, W.V. Aust. J. Chem. 1976, 29, 1365.
12. Vesonder, R.F, Stodola, F.H., Wickerham, L.J., Ellis, J.J. and Rolwedder, W.K. Can. J. Chem. 1971, 49, 2029.
13. Mason, T.J. and Lorimer, J.P. "Sonochemistry: Theory, Applications and uses of Ultrasound in Chemistry", Ellis Horwood Limited, Chichester, 1988, p. 91.
14. Larock, R.C., "Comprehensive Organic Transformations: Guide to Fundamental Group Preparations", VCH, Weinheim/New York, 1989; Isomerization of Alkenes.
15. Sonnet, P.E. J.Org. Chem. 1980, 45, 154
16. Sonnet, P.E. J.Org. Chem. 1974, 39, 3793.
17. Resck, I.S. and Mahajan, J.R., 6th Brazilian Meeting on Organic Synthesis, 1994; ABSTRACTS, p. 69.
18. Some earlier syntheses of recifeiolide: (a) Corey, E.J., Ulrich, P. Fitzpatrick, J.M. J. Am. Chem. Soc. 1976, 98, 222; (b) Gerlach, H., Oertle, K. and Thalmann, A. Helv. Chim. Acta 1976, 59, 755; (c) Trost, B.M. and Verhoeven, T.R. Tetrahedron Lett. 1978, 2275; J..Am.Chem.Soc 1980, 102, 4743; (d) Wasserman, H.H., Gambale, R.J. and Pulwer, M.J. Tetrahedron 1981, 37, 4059.
19. Some earlier syntheses of recifeiolide: (a) Corey, E.J., Ulrich, P. Fitzpatrick, J.M. J. Am. Chem. Soc. 1976, 98, 222; (b) Gerlach, H., Oertle, K. and Thalmann, A. Helv. Chim. Acta 1976, 59, 755; (c) Trost, B.M. and Verhoeven, T.R. Tetrahedron Lett. 1978, 2275; J..Am.Chem.Soc 1980, 102, 4743; (d) Wasserman, H.H., Gambale, R.J. and Pulwer, M.J. Tetrahedron 1981, 37, 4059.
20. Some earlier syntheses of recifeiolide: (a) Corey, E.J., Ulrich, P. Fitzpatrick, J.M. J. Am. Chem. Soc. 1976, 98, 222; (b) Gerlach, H., Oertle, K. and Thalmann, A. Helv. Chim. Acta 1976, 59, 755; (c) Trost, B.M. and Verhoeven, T.R. Tetrahedron Lett. 1978, 2275; J..Am.Chem.Soc 1980, 102, 4743; (d) Wasserman, H.H., Gambale, R.J. and Pulwer, M.J. Tetrahedron 1981, 37, 4059.
21. Some earlier syntheses of recifeiolide: (a) Corey, E.J., Ulrich, P. Fitzpatrick, J.M. J. Am. Chem. Soc. 1976, 98, 222; (b) Gerlach, H., Oertle, K. and Thalmann, A. Helv. Chim. Acta 1976, 59, 755; (c) Trost, B.M. and Verhoeven, T.R. Tetrahedron Lett. 1978, 2275; J..Am.Chem.Soc 1980, 102, 4743; (d) Wasserman, H.H., Gambale, R.J. and Pulwer, M.J. Tetrahedron 1981, 37, 4059.
22. Some earlier syntheses of recifeiolide: (a) Corey, E.J., Ulrich, P. Fitzpatrick, J.M. J. Am. Chem. Soc. 1976, 98, 222; (b) Gerlach, H., Oertle, K. and Thalmann, A. Helv. Chim. Acta 1976, 59, 755; (c) Trost, B.M. and Verhoeven, T.R. Tetrahedron Lett. 1978, 2275; J..Am.Chem.Soc 1980, 102, 4743; (d) Wasserman, H.H., Gambale, R.J. and Pulwer, M.J. Tetrahedron 1981, 37, 4059.
23. Mahajan, J.R. and Resck, I.S., unpublished results.
24. Mahajan, J.R., Resck, I.S., Braz-filho, R. and Carvalho, M.G., 5th Meeting of NMR Users, Angra dos Reis - RJ, 1995; ABSTRACTS, p .38.