Fe(III)/Cu(II) mediated 5- and 6-exo oxidative ring expansion/cyclisation of cyclopropyl ethers: Studies towards dictyol C and α-eudesmol

Tetrahedron Letters

Volumn 41, Issue 23, 2000, Pages 4651-4655

  Booker Milburn, Kevin I ^a   Cox, Brian ^b   Grady, Mick ^a   Halley, Frank ^c   Marrison, Shaun ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

^c Aventis Pharma Ltd   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA EUDESMOL; COPPER ION; CYCLOPROPANE DERIVATIVE; DICTYOL C; ETHER DERIVATIVE; FERRIC ION; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; OXIDATION; REACTION ANALYSIS;

EID: 0034640849     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00648-1     Document Type: Article

References (13)

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2. Booker-Milburn, K. I.; Barker, A.; Brailsford, W.; Cox, B.; Mansley, T. E. Tetrahedron 1998, 54, 15321.
3. Enoki, N.; Tsuzuki, K.; Omura, S.; Ishida, R. Chem. Lett. 1983, 1627.
4. (a) Humber, D. C.; Pinder, A. R. Tetrahedron Lett. 1966, 41, 4985;
5. (b) Frey, B.; Hunig, S.; Koch, M.; Reissig, H. Synlett 1991, 854.
6. Rigby, J. H.; Wilson, J. Z. J. Am. Chem. Soc. 1984, 106, 8217.
7. (a) de la Mare, H. E.; Kochi, J. K.; Rust, F. F. J. Am. Chem. Soc. 1963, 85, 1437;
8. (b) Kochi, J. K. Acc. Chem. Res. 1974, 7, 351.
9. Snider, B. B.; Vo, N. H.; Foxman, B. M. Chem. Rev. 1996, 96, 339.
10. For previous examples of 6-exo cyclisations of cyclopropane derived radicals, see: (a) Iwasawa, N.; Funahashi, M.; Hayakawa, S.; Narasaka, K. Chem. Lett. 1993, 545;
11. (b) Booker-Milburn, K. I.; Dainty, R. F. Tetrahedron Lett. 1998, 39, 5097;
12. (c) Blake, A. J.; Highton, A. J.; Majid, T. N.; Simpkins, N. J. Org. Lett. 1999, 1, 1787.
13. 2. Evidence was given in support of a non-radical mechanism in these cases: Ryu, I.; Matsumoto, K.; Kameyama, Y.; Ando, M.; Kusumoto, N.; Ogawa, A.; Kambe, N.; Murai, S.; Sonoda, N. J. Am. Chem. Soc. 1993, 115, 12330.