Radical dearomatising spirocyclisations onto the C-2 position of benzofuran and indole

Tetrahedron Letters

Volumn 45, Issue 48, 2004, Pages 8931-8934

  Kyei, Afua S ^a   Tchabanenko, Kirill ^a   Baldwin, Jack E ^a   Adlington, Robert M ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

Alkyl radical; Aryl radical; Benzofuran; Indole; Spirocycle; Spirocyclisation; Vinyl radical

Indexed keywords

ANTINEOPLASTIC AGENT; BENZOFURAN DERIVATIVE; INDOLE DERIVATIVE;

ARTICLE; CHEMICAL REACTION KINETICS; CYCLIZATION; DRUG SYNTHESIS; FRAGMENTATION REACTION; MOLECULAR INTERACTION; QUANTUM YIELD; RADICAL DEAROMATISING SPIROCYCLISATION; REACTION ANALYSIS; SUBSTITUTION REACTION;

EID: 7444263977     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.09.148     Document Type: Article

References (24)

1. B.D. Morris, and M.R. Prinsep J. Nat. Prod. 62 1999 688 693
2. H. Takayama, M. Kurihara, S. Subhadhirasakul, M. Kitajima, N. Aimi, and S.-I. Sakai Heterocycles 42 1996 87 92
3. H. Takayama, H. Ishikawa, M. Kurihara, M. Kitajima, N. Aimi, D. Ponglux, F. Koyama, K. Matsumoto, T. Moriyama, L.T. Yamamoto, and K. Watanabe J. Med. Chem. 45 2002 1949 1956
4. N.S. Narasimhan, and I.S. Aidhen Tetrahedron Lett. 29 1988 2987 2988
5. J.C. Estevez, M.C. Villaverde, R.J. Estevez, and L. Castedo Heterocycles 38 1994 1 4
6. J.C. Estevez, M.C. Villaverde, R.J. Estevez, and L. Castedo Tetrahedron 50 1994 2107 2114
7. S. Caddick, K. Aboutayab, and R.I. West Chem. Commun. 13 1995 1353 1354
8. S. Caddick, K. Aboutayab, K. Jenkins, and R.I. West J. Chem. Soc., Perkin Trans. 1 7 1996 675 682
9. E. Bonfand, L. Forslund, W.B. Motherwell, and S. Vazquez Synlett 2000 475 478
10. H. Ohno, R. Wakayama, S.-I. Maedo, H. Iwasaki, M. Okumura, C. Iwata, H. Mikamiyama, and T. Tanaka J. Org. Chem. 65 2003 5909 5916
11. D.C. Harrowven, N. L'Helias, J.D. Moseley, N.J. Blumire, and S.R. Flanagan Chem. Commun. 21 2003 2658 2659
12. J. Boivin, M. Yousfi, and S.Z. Zard Tetrahedron Lett. 38 1997 5985 5988
13. P.J. Parsons, M. Penverne, and I.L. Pinto Synlett 1994 721 722
14. A. Demircan, and P.J. Parsons Synlett 1998 1215 1216
15. P. Jones, W.-S. Li, G. Pattenden, and N.M. Thomson Tetrahedron Lett. 38 1997 9072 9096
16. K. Jones, T.C.T. Ho, and J. Wilkinson Tetrahedron Lett. 36 1995 6743 6744
17. T.C.T. Ho, and K. Jones Tetrahedron 53 1997 8287 8294
18. C. Escolano, and K. Jones Tetrahedron Lett. 41 2000 8951 8955
19. C. Escolano, and K. Jones Tetrahedron 58 2002 1453 1464
20. S.T. Hilton, T.C.T. Ho, G. Pljevaljcic, M. Schulte, and K. Jones Org. Lett. 2 2000 2639 2641
21. S.T. Hilton, T.C.T. Ho, G. Pljevaljcic, M. Schulte, and K. Jones Chem. Commun. 2001 209 210
22. 2 requires 252.1025
23. The use of alkyl selenides for the radical cyclisations had an extra advantage. Thiophenol was not required in the workup as the byproduct tributyltin phenylselenide was easily separable by column chromatography
24. R.M. Adlington, and A.G.M. Barrett J. Chem. Soc., Perkin Trans. 1 1981 2848 2863