Studies in bromoacetylenic oxy-Cope rearrangement: Synthesis of functionalised medium-size, bicyclic and angularly fused tricyclic compounds

Tetrahedron

Volumn 53, Issue 37, 1997, Pages 12637-12650

  Shanmugam, Ponnusamy ^b   Devan, Balachari ^c   Srinivasan, Rajagopal ^a   Rajagopalan, Krishnamoorthy ^a  

^a UNIVERSITY OF MADRAS   (India)

^b REGIONAL RESEARCH LABORATORY CSIR   (India)

^c UNIVERSITY OF NEW ORLEANS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC HYDROCARBON;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

OXY;

EID: 0030750955     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00785-0     Document Type: Article

References (31)

1. (a) Paquette, L. A.; Doherty, A. M. In Polyquinane Chemistry: Reactivity and Structure Concepts in Organic Chemistry; Springer-Verlag: Berlin. 1989, Vol. 26.
2. (b) Sticher, O. in "New Natural Products and Plant Drugs with Pharmalogical, Biological or Therapeutic Activity", ed. Wagner, G.; Woff, P. Springer-Verlag, Berlin, 1977.
3. (c) HeathCock, C.H. in "Synthesis of Natural Products", ed. Apsimon, T. Wiley, New York, 1973, vol.2 and vol. 5.
4. (d) Porter, L. Chem. Rev., 1967, 67, 441
5. (e) Hudlicky, T.; Kutchan, T.T.; Wilson, S.R.; Mao, D.T. J. Am. Chem. Soc., 1980, 102, 6351.
6. (a) Lutz, R.P. Chem. Rev., 1984, 84, 205 and references cited therein.
7. (b) Paquette, L. A. Angew. Chem. Intern. Edn. (Eng). 1990, 20, 609.
8. (c) Herdon, J.W.; Mc Millan, L. A.; Daitch, C.E. Tetrahedron Lett., 1990, 31, 4547.
9. (a) Snider, B.B. in "Comprehensive Organic Synthesis", ed. Trost, B.M.; Fleming, I. Pergamon Press, Oxford, 1991, vol.2, pp 527-561; vol.3, pp 379; vol.1, pp 880.
10. (a) Snider, B.B. in "Comprehensive Organic Synthesis", ed. Trost, B.M.; Fleming, I. Pergamon Press, Oxford, 1991, vol.2, pp 527-561; vol.3, pp 379; vol.1, pp 880.
11. (a) Snider, B.B. in "Comprehensive Organic Synthesis", ed. Trost, B.M.; Fleming, I. Pergamon Press, Oxford, 1991, vol.2, pp 527-561; vol.3, pp 379; vol.1, pp 880.
12. (b) Lorenc, L.; Raj Kovic, M.; Miloranovic, A.; Mihailovic, M. J. Chem. Soc., Perkin Trans. 1, 1988, 1495.
13. (c) Mez, H.G.; Rist, G.; Ermer, O.; Lorenc, L.; Kalvoda, J.; Mihailovic, M. Tetrahedron, 1990, 46, 3659.
14. (d) Still, W.C. J. Am. Chem. Soc., 1977, 99, 4186. ibid., 1979, 101, 493.
15. (d) Still, W.C. J. Am. Chem. Soc., 1977, 99, 4186. ibid., 1979, 101, 493.
16. (e) Clive, D.L.J.; Russel, C.G.; Suri, S.C. J. Org. Chem., 1982, 47, 1632.
17. (f) Kato, T.; Kondo, H.; Nishino, M.; Tanaka, M.; Hata, G.; Miyaka, A. Bull. Chem. Soc. Jpn., 1980, 53, 2925.
18. (a) Janardhanam, S.; Devan, B.; Rajagopalan, K. Tetrahedron Lett., 1993, 34, 6761.
19. (b) Janardhanam, S.; Rajagopalan, K. J. Chem. Soc., Perkin Trans. 1, 1992, 2727.
20. (c) Janardhanam, S.; Shanmugam, P.; Rajagopalan, K. Synth. Commun., 1993, 23, 311.
21. (d) Balakumar, A.; Janardhanam, S.; Rajagopalan, K. J. Org. Chem., 1993, 58, 5482.
22. (e) Shanmugam, P.; Rajagopalan, K. Synth Commun., 1996, 26, 2119.
23. (f) Shanmugam, P.; Rajagopalan, K. Tetrahedron, 1996, 52, 7737.
24. Hofmeister, H.; Annen, K.; Laurent, H.; Wiechert, R. Angew. Chem. Int. Ed. Eng. 1984, 23, 727.
25. (a) Ramachandran, S.; Newman, M. S. Org. Synth., Col. Vol. IV, 553.
26. (b) Balakumar, A. "Claisen and Allenic oxy-Cope Rearrangements" Ph. D Thesis, University of Madras, December, 1992.
27. Izhal, R. R.; Fencal, W.; Brucetagle,; Clardy, J. Tetrahedron, 1981, 37, 2569.
28. Bohlmann, F.; Zdero, C. Chem. Ber., 1977, 110, 468.
29. Eaton, P. E.; Jobbe, P. G. Synthesis, 1983, 796.
30. Ravikumar, V. T.; Rajagopalan, K.; Swaminathan, S. Tetrahedron Lett, 1985, 26, 6137.
31. Perrin, D.D.; Armarego, W.L.F. Purification of Laboratory Chemicals, 3rd edn; Pergamon Press, New York, 1988.