Novel cascade of seven radical-mediated 6-endo-tng cyclisations leading to a unique a\\-trans, anti heptacycle

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 8, 1999, Pages 843-845

  Handa, Sandeep ^a   Pattenden, Gerald ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001306618     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a901079c     Document Type: Article

References (12)

1. See for example, (a) L. Chen, G. B. Gill, G. Pattenden and H. Simonian, J. Client. Soc., Perkin Trans. I, 1996, 31; Reference 7 below; and extensive bibliography contained in these publications;
2. (b) S. A. Hitchcock, S. J. Houldsworth, G. Pattenden, D. C. Pryde, N. M. Thomson and A. J. Blake, J. Client. Soc., Perkin Traits. 1,1998, 3181;
3. G. J. Hollingworth, G. Pattenden and D. J. Schulz, Aiist. J. Client., 1995, 48, 381;
4. S. Manda and G. Pattenden, Client. Commun., 1998, 311; S. Handa and G. Pattenden, Cuntcmp. Org. Synllt., 1997,4, 196.
5. For a similar strategy for the synthesis of the octaprenol 3c sec: (a) K. Sato, S. Inoue, A. Onishi, N. Uchida and N. Minowa, J. Client. Soc., Perkin Trans. 1, 1981, 761;
6. ( b) E. E. van Tamelen and S. A. Marson, Bioorg. Client., 1982, 11, 219.
7. All new compounds displayed satisfactory spectroscopic data together with microanalytical and/or mass spcctrometric data.
8. 2OH), 5.13-5.10 (2H, m, 2 x C=CH), 4.16 (2H, d, J 6.7 Hz, Ctf2OH), 2.27-0.80 (complex series of multiplets), 1.68 (3H, s, C=C(CH,)), 1.60 (6H, s, 2 x C=C(CH3)), 0.91 (3H, d, J 7.1 Hz, CHCHj), 0.86 (3H, s, CH3), 0.85 (3H, s, CH3), 0.84 (3H, s, CH,);<5C(125.8 MHz; CDC1,) 213.8 (s), 139.8 (s), 135.4 (s), 135.0 (s), 124.2 (d), 123.7 (d), 123.3 (d), 65.8 (t), 61.4 (d), 61.1 (d), 59.7 (d), 51.9 (d), 43.4 (s), 42.0 (t), 41.8 (t), 40.8 (t), 39.7 (t), 39.5 (t), 38.1 (t), 38.0 (t), 37.7 (t), 37.5 (s), 37.4 (s), 30.3 (d), 26.6 (t), 26.3 (t), 22.3 (t), 21.4 (t), 17.3 (2 x q), 17.1 (3 x t), 16.3 ' (q), 16.0 (q), 15.9 (q), 15.3 (q) and 13.8 (q); ml: (El) 532.4669 (M+ - H A CjgH-4O requires 532.4644).
9. D. S. de Miranda, G. Brendolan, P. M. Imamura, M. Gonzalez Sierra, A. J. Marsaioli and E. A. Ruveda, J. Org. Chem., 1981, 46, 4851.
10. H. Beierbeck, J. K. Saunders and J. W. Apsimon, Can. J. Chem., 1977, 55, 2813; H. Beierbeck and J. K. Saunders, Can. J. Chem., 1975, 53, 1307.
11. For a similar I3C NMR based analysis of the stereochemistry of fused cyclohexane system? see: A. Batsanov, L. Chen, G. B. Gill and G. Pattenden, J. Chem. Soc.,'Pcrkin Trans. I, 1996,45.
12. For some novel polycyclisations using the Heck reaction leading to penta- and heptacycles see: T. Sighihara, C. Coperet, Z. Owczarczyk, L. S. Harding and E. Negishi, J. Am. Chem. Soc., 1994, 116, 7923; B. M. Trost and Y. Shi, J. Am. Chem. Soc., 1993,115,9421.