Cascade radical cyclisations with vinylcyclopropane electrophores

Tetrahedron Letters

Volumn 38, Issue 20, 1997, Pages 3647-3650

  Pattenden, Gerald ^a   Wiedenau, Paul ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

MACROCYCLIC COMPOUND; POLYCYCLIC HYDROCARBON;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030971741     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00691-6     Document Type: Article

References (16)

1. See for example :Jasperse, C.P.; Curran, D.P.; Fevig, T.L. Chem. Rev. 1991, 91, 1237.
2. Hitchcock, S.A.; Pattenden, G. Tetrahedron Lett. 1992, 33, 4843. Pattenden, G.; Smithies, A.J.; Tapolczay, D.; Walter, D.S. J. Chem. Soc., Perkin Trans. 1 1996, 7 and 21 and references cited therein. Blake, A.J.; Hollingworth, G.J.; Pattenden, G. Synlett 1996, 643.
3. Hitchcock, S.A.; Pattenden, G. Tetrahedron Lett. 1992, 33, 4843. Pattenden, G.; Smithies, A.J.; Tapolczay, D.; Walter, D.S. J. Chem. Soc., Perkin Trans. 1 1996, 7 and 21 and references cited therein. Blake, A.J.; Hollingworth, G.J.; Pattenden, G. Synlett 1996, 643.
4. Hitchcock, S.A.; Pattenden, G. Tetrahedron Lett. 1992, 33, 4843. Pattenden, G.; Smithies, A.J.; Tapolczay, D.; Walter, D.S. J. Chem. Soc., Perkin Trans. 1 1996, 7 and 21 and references cited therein. Blake, A.J.; Hollingworth, G.J.; Pattenden, G. Synlett 1996, 643.
5. Porter, N.A.; Chang, V.H.-T. J. Am. Chem. Soc. 1987, 109, 4976.
6. Curran, D.P. in Comprehensive Organic Synthesis, Vol. 4, 715; Trost, B.M.; Fleming, I., Ed.; Pergamon Press 1991.
7. Wong, H.N.C.; Moon-Yuen, H.; Chun-Wah, T.; Yu-Chip, Y.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165.
8. All new compounds displayed satisfactory spectroscopic data together with microanalytical and/or mass spectrometric data.
9. For the use of TTMSS as a non-toxic alternative to tin hydrides in radical reactions see: Giese, B.; Kopping, B.; Chatgilialoglu, C. Tetrahedron Lett. 1989, 30, 681. Ballestri, M.; Chatgilialoglu, C.; Clark, K.B.; Griller, D.; Giese, B.; Kopping, B. J. Org. Chem. 1991, 56, 678. Chatgilialoglu, C. Acc. Chem. Res. 1992, 25, 188.
10. For the use of TTMSS as a non-toxic alternative to tin hydrides in radical reactions see: Giese, B.; Kopping, B.; Chatgilialoglu, C. Tetrahedron Lett. 1989, 30, 681. Ballestri, M.; Chatgilialoglu, C.; Clark, K.B.; Griller, D.; Giese, B.; Kopping, B. J. Org. Chem. 1991, 56, 678. Chatgilialoglu, C. Acc. Chem. Res. 1992, 25, 188.
11. For the use of TTMSS as a non-toxic alternative to tin hydrides in radical reactions see: Giese, B.; Kopping, B.; Chatgilialoglu, C. Tetrahedron Lett. 1989, 30, 681. Ballestri, M.; Chatgilialoglu, C.; Clark, K.B.; Griller, D.; Giese, B.; Kopping, B. J. Org. Chem. 1991, 56, 678. Chatgilialoglu, C. Acc. Chem. Res. 1992, 25, 188.
12. Structures were assigned on the basis of NMR data from DQF-COSY, homodecoupling and NOE experiments.
13. The tricyclic ketone 7 was produced from the radical cyclisation of the diene selenyl ester shown below, using similar chemistry to that already published for the homologous (6,6,6-fused) tricyclic system; see Ligong, C.; Gill, G.B.; Pattenden, G.; Simonian, H. J. Chem. Soc., Perkin Trans.1 1996, 31.
14. Curley, Jr, R.W.; Deluca, H.F. J. Org. Chem. 1984, 49, 1941.
15. Still, W.C.; Macromodel (version 4.0), Columbia University, NY, 1993.
16. 11 suggest that the first transannular cyclisation from 13 is sterically hindered by the rigidity of the fused benzene ring in the intermediate.