Radical Mediated Macrocyclisation-Transannulation Cascades leading to Ring-fused Lactones and Lactams

Synlett

Volumn 1996, Issue 7, 1996, Pages 643-644

  Blake, Alexander J ^a   Hollingworth, Gregory J ^a   Pattenden, Gerald ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002789123     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5558     Document Type: Article

References (19)

1. For examples of cascade electrophilic cyclisations, see: Sutherland, J.K.; 'Polyene Cyclisations' in Comprehensive Organic Synthesis, vol 3, 341, ed. B.M. Trost, Pergamon 1991; Taylor S.K.; Org. Prep. Proced. Int., 1992, 24, 245. Fish, P.V., Sudhakar, A.R. and Johnson, W.S.; Tetrahedron Lett., 1993, 34, 7849. For a transition metal-mediated cascade see: Snider, B.B., Mohan, R. and Kates, S.A.; J. Org. Chem., 1985, 50, 3659. For other radical cascades see; Jasperse, C.P., Curran, D.P. and Fevig, T.L.; Chem Rev., 1991, 91, 1237. For examples of pericyclic cascades from polyene precursors, see: Mulzer, J., Bock, H., Eck, W., Buschmann, J. and Luger, P., Angew. Chem., Int. Ed. Eng., 1991, 30, 414. Raucher, S., Chi, K.-W., Hwang, K.-J. and Burks Jr., J.E., J. Org. Chem., 1986, 51, 5503.
2. For examples of cascade electrophilic cyclisations, see: Sutherland, J.K.; 'Polyene Cyclisations' in Comprehensive Organic Synthesis, vol 3, 341, ed. B.M. Trost, Pergamon 1991; Taylor S.K.; Org. Prep. Proced. Int., 1992, 24, 245. Fish, P.V., Sudhakar, A.R. and Johnson, W.S.; Tetrahedron Lett., 1993, 34, 7849. For a transition metal-mediated cascade see: Snider, B.B., Mohan, R. and Kates, S.A.; J. Org. Chem., 1985, 50, 3659. For other radical cascades see; Jasperse, C.P., Curran, D.P. and Fevig, T.L.; Chem Rev., 1991, 91, 1237. For examples of pericyclic cascades from polyene precursors, see: Mulzer, J., Bock, H., Eck, W., Buschmann, J. and Luger, P., Angew. Chem., Int. Ed. Eng., 1991, 30, 414. Raucher, S., Chi, K.-W., Hwang, K.-J. and Burks Jr., J.E., J. Org. Chem., 1986, 51, 5503.
3. For examples of cascade electrophilic cyclisations, see: Sutherland, J.K.; 'Polyene Cyclisations' in Comprehensive Organic Synthesis, vol 3, 341, ed. B.M. Trost, Pergamon 1991; Taylor S.K.; Org. Prep. Proced. Int., 1992, 24, 245. Fish, P.V., Sudhakar, A.R. and Johnson, W.S.; Tetrahedron Lett., 1993, 34, 7849. For a transition metal-mediated cascade see: Snider, B.B., Mohan, R. and Kates, S.A.; J. Org. Chem., 1985, 50, 3659. For other radical cascades see; Jasperse, C.P., Curran, D.P. and Fevig, T.L.; Chem Rev., 1991, 91, 1237. For examples of pericyclic cascades from polyene precursors, see: Mulzer, J., Bock, H., Eck, W., Buschmann, J. and Luger, P., Angew. Chem., Int. Ed. Eng., 1991, 30, 414. Raucher, S., Chi, K.-W., Hwang, K.-J. and Burks Jr., J.E., J. Org. Chem., 1986, 51, 5503.
4. For examples of cascade electrophilic cyclisations, see: Sutherland, J.K.; 'Polyene Cyclisations' in Comprehensive Organic Synthesis, vol 3, 341, ed. B.M. Trost, Pergamon 1991; Taylor S.K.; Org. Prep. Proced. Int., 1992, 24, 245. Fish, P.V., Sudhakar, A.R. and Johnson, W.S.; Tetrahedron Lett., 1993, 34, 7849. For a transition metal-mediated cascade see: Snider, B.B., Mohan, R. and Kates, S.A.; J. Org. Chem., 1985, 50, 3659. For other radical cascades see; Jasperse, C.P., Curran, D.P. and Fevig, T.L.; Chem Rev., 1991, 91, 1237. For examples of pericyclic cascades from polyene precursors, see: Mulzer, J., Bock, H., Eck, W., Buschmann, J. and Luger, P., Angew. Chem., Int. Ed. Eng., 1991, 30, 414. Raucher, S., Chi, K.-W., Hwang, K.-J. and Burks Jr., J.E., J. Org. Chem., 1986, 51, 5503.
5. For examples of cascade electrophilic cyclisations, see: Sutherland, J.K.; 'Polyene Cyclisations' in Comprehensive Organic Synthesis, vol 3, 341, ed. B.M. Trost, Pergamon 1991; Taylor S.K.; Org. Prep. Proced. Int., 1992, 24, 245. Fish, P.V., Sudhakar, A.R. and Johnson, W.S.; Tetrahedron Lett., 1993, 34, 7849. For a transition metal-mediated cascade see: Snider, B.B., Mohan, R. and Kates, S.A.; J. Org. Chem., 1985, 50, 3659. For other radical cascades see; Jasperse, C.P., Curran, D.P. and Fevig, T.L.; Chem Rev., 1991, 91, 1237. For examples of pericyclic cascades from polyene precursors, see: Mulzer, J., Bock, H., Eck, W., Buschmann, J. and Luger, P., Angew. Chem., Int. Ed. Eng., 1991, 30, 414. Raucher, S., Chi, K.-W., Hwang, K.-J. and Burks Jr., J.E., J. Org. Chem., 1986, 51, 5503.
6. For examples of cascade electrophilic cyclisations, see: Sutherland, J.K.; 'Polyene Cyclisations' in Comprehensive Organic Synthesis, vol 3, 341, ed. B.M. Trost, Pergamon 1991; Taylor S.K.; Org. Prep. Proced. Int., 1992, 24, 245. Fish, P.V., Sudhakar, A.R. and Johnson, W.S.; Tetrahedron Lett., 1993, 34, 7849. For a transition metal-mediated cascade see: Snider, B.B., Mohan, R. and Kates, S.A.; J. Org. Chem., 1985, 50, 3659. For other radical cascades see; Jasperse, C.P., Curran, D.P. and Fevig, T.L.; Chem Rev., 1991, 91, 1237. For examples of pericyclic cascades from polyene precursors, see: Mulzer, J., Bock, H., Eck, W., Buschmann, J. and Luger, P., Angew. Chem., Int. Ed. Eng., 1991, 30, 414. Raucher, S., Chi, K.-W., Hwang, K.-J. and Burks Jr., J.E., J. Org. Chem., 1986, 51, 5503.
7. For examples of cascade electrophilic cyclisations, see: Sutherland, J.K.; 'Polyene Cyclisations' in Comprehensive Organic Synthesis, vol 3, 341, ed. B.M. Trost, Pergamon 1991; Taylor S.K.; Org. Prep. Proced. Int., 1992, 24, 245. Fish, P.V., Sudhakar, A.R. and Johnson, W.S.; Tetrahedron Lett., 1993, 34, 7849. For a transition metal-mediated cascade see: Snider, B.B., Mohan, R. and Kates, S.A.; J. Org. Chem., 1985, 50, 3659. For other radical cascades see; Jasperse, C.P., Curran, D.P. and Fevig, T.L.; Chem Rev., 1991, 91, 1237. For examples of pericyclic cascades from polyene precursors, see: Mulzer, J., Bock, H., Eck, W., Buschmann, J. and Luger, P., Angew. Chem., Int. Ed. Eng., 1991, 30, 414. Raucher, S., Chi, K.-W., Hwang, K.-J. and Burks Jr., J.E., J. Org. Chem., 1986, 51, 5503.
8. Ho, T.-L.; 'Tandem Organic Reactions', Wiley, NY, 1992. For a review, see: Tietze, L.F. and Beifuss, U.; Angew. Chem., Int. Ed. Eng., 1993, 32, 131.
9. Ho, T.-L.; 'Tandem Organic Reactions', Wiley, NY, 1992. For a review, see: Tietze, L.F. and Beifuss, U.; Angew. Chem., Int. Ed. Eng., 1993, 32, 131.
10. Pattenden, G., Smithies, A.J., Tapolczay, D. and Walter D.S; J. Chem. Soc., Perkin Trans. 1, 1996, 7. Begley, M.J., Pattenden, G., Smithies, A.J., Tapolczay, D. and Walter D.S; J. Chem. Soc., Perkin Trans. 1, 1996, 21 and references cited therein. Hitchcock, S.A. and Pattenden G.; Tetrahedron Lett., 1992, 33, 4843.
11. Pattenden, G., Smithies, A.J., Tapolczay, D. and Walter D.S; J. Chem. Soc., Perkin Trans. 1, 1996, 7. Begley, M.J., Pattenden, G., Smithies, A.J., Tapolczay, D. and Walter D.S; J. Chem. Soc., Perkin Trans. 1, 1996, 21 and references cited therein. Hitchcock, S.A. and Pattenden G.; Tetrahedron Lett., 1992, 33, 4843.
12. Pattenden, G., Smithies, A.J., Tapolczay, D. and Walter D.S; J. Chem. Soc., Perkin Trans. 1, 1996, 7. Begley, M.J., Pattenden, G., Smithies, A.J., Tapolczay, D. and Walter D.S; J. Chem. Soc., Perkin Trans. 1, 1996, 21 and references cited therein. Hitchcock, S.A. and Pattenden G.; Tetrahedron Lett., 1992, 33, 4843.
13. Hollingworth, G.J., Pattenden, G. and Schulz, D.J.; Aust. J. Chem., 1995, 48, 381 and references cited therein.
14. Chen, L., Gill, G.B., Pattenden, G. and Siraonian, H., J. Chem. Soc., Perkin Trans. 1, 1996, 31. Batsanov, A., Chen, L., Gill, G.B.and Pattenden, G.; J. Chem. Soc., Perkin Trans. 1, 1996, 45 and references cited therein.
15. Chen, L., Gill, G.B., Pattenden, G. and Siraonian, H., J. Chem. Soc., Perkin Trans. 1, 1996, 31. Batsanov, A., Chen, L., Gill, G.B.and Pattenden, G.; J. Chem. Soc., Perkin Trans. 1, 1996, 45 and references cited therein.
16. For a tandem radical cyclisation process involving ring closure onto an imine, see: Bowman, W.R., Stephenson, P.T. and Young, A.R.; Tetrahedron Lett., 1995, 36, 5623.
17. 19NO requires 181.14665, 181 (70%), 126 (19%), 109 (35%), 98 (100%), 67 (31).
18. Satisfactory spectroscopic data together with mass spectrometry and/or microanalytical data were obtained for all new compounds. Crystallographic data have been deposited with the Cambridge Crystallographic Data Centre.
19. For an attempted formation of a 12-membered lactone by radical macrocyclisation of a propiolate ester, see: Baldwin, J.E., Adlington, R.M. and Ramcharitar, S.H.; Tetrahedron, 1992, 48, 3413.