Phosphonyl radical addition to enol ethers. The stereoselective synthesis of cyclic ethers

Tetrahedron Letters

Volumn 45, Issue 26, 2004, Pages 5095-5098

  Jessop, Christopher M ^a   Parsons, Andrew F ^a   Routledge, Anne ^a   Irvine, Derek J ^b  

^a UNIVERSITY OF YORK   (United Kingdom)

^b Wilton Centre   (United Kingdom)

Author keywords

Cyclisation; Phosphorus compounds; Radicals and radical reactions

Indexed keywords

ETHER DERIVATIVE; ORGANOPHOSPHATE; PHOSPHITE; PHOSPHONIC ACID DERIVATIVE; TETRAHYDROFURAN DERIVATIVE; THIOL DERIVATIVE; VINYL DERIVATIVE;

ADDITION REACTION; ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; DIASTEREOISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS; WITTIG REACTION;

EID: 2942534474     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.04.173     Document Type: Article

References (41)

1. See, for example: Deprèle S., Montchamp J.-L. J. Org. Chem. 66:2001;6745-6755
2. Herpin T.F., Motherwell W.B., Roberts B.P., Roland S., Weibel J.-M. Tetrahedron. 53:1997;15085-15100
3. Lopin C., Gautier A., Gouhier G., Piettre S.R. Tetrahedron Lett. 41:2000;10195-10200
4. Dubert O., Gautier A., Condamine E., Piettre S.R. Org. Lett. 4:2002;359-362
5. Piettre S.R. Tetrahedron Lett. 37:1996;2233-2236
6. Piettre S.R. Tetrahedron Lett. 37:1996;4707-4710
7. Rey P., Taillades J., Rossi J.C., Gros G. Tetrahedron Lett. 44:2003;6169-6171
8. Jessop C.M., Parsons A.F., Routledge A., Irvine D. Tetrahedron Lett. 44:2003;479-483
9. Gautier A., Garipova G., Dubert O., Oulyadi H., Piettre S.R. Tetrahedron Lett. 42:2001;5673-5676
10. Trofimov B.A., Khil'ko M.Y., Nedolya N.A., Vyalykh E.P. J. Org. Chem. USSR (Engl. Transl.). 17:1981;1038-1040
11. Brel' A.K., Tyurenkov I.N., Strel'tsova G.V., Matyukhova N.P., Nazarenko V.N., Agarkova N.S. Pharm. Chem. J. (Engl. Transl.). 22:1988;118-120
12. Nishiwaki T. Tetrahedron. 21:1965;3043-3049
13. See, for example: Diana G.D., Zalay E.S., Salvador U.J., Pancic F., Steinberg B. J. Med. Chem. 27:1984;691-694
14. Yoshino K., Kohno T., Morita T., Tsukamoto G. J. Med. Chem. 32:1989;1528-1532
15. Kelley J.L., Linn J.A., McLean E.W., Tuttle J.V. J. Med. Chem. 36:1993;3455-3463
16. Hakimelahi G.H., Moosavi-Movahedi A.A., Sadeghi M.M., Tsay S.-C., Hwu J.R. J. Med. Chem. 38:1995;4648-4659
17. Liu H., Li W., Kim C.U. Bioorg. Med. Chem. Lett. 7:1997;1419-1420
18. Cermak D.M., Wiemer D.F., Lewis K., Hohl R.J. Bioorg. Med. Chem. 8:2000;2729-2737
19. Williams D.M., Jakeman D.L., Vyle J.S., Williamson M.P., Blackburn G.M. Bioorg. Med. Chem. Lett. 8:1998;2603-2608
20. All new compounds gave consistent spectral and high resolution mass spectroscopic data
21. +, 239.1412
22. Gurjar M.K., Krishna L.M., Reddy B.S., Chorghade M.S. Synthesis. 2000;557-560
23. Ghosh S., Raychaudhuri S.R., Salomon R.G. J. Org. Chem. 52:1987;83-90
24. Nakajima R., Urabe H., Sato F. Chem. Lett. 2002;4-5
25. McMurry J.E., Kocovsky P. Tetrahedron Lett. 26:1985;2171-2172
26. For related alkoxymethyl radical cyclisations, see: Rawal V.H., Singh S.P., Dufour C., Michoud C. J. Org. Chem. 58:1993;7718-7727
27. Lolkema L.D.M., Hiemstra H., Al Ghouch A.A., Speckamp W.N. Tetrahedron Lett. 32:1991;1491-1494
28. For the major diastereoisomer of 15, a correlation between H6 and the C-5 methyl group was observed in the NOESY spectrum. Correlations between H2 and H6 were observed for both isomers of 15, which suggest that the minor diastereoisomers of 15 and 17 have the all cis-stereochemistry
29. Keller-Juslén C., King H.D., Kuhn M., Loosli H.-R., Pache W., Petcher T.J., Weber H.P., Wartburg A. J. Antibiot. 35:1982;142-150
30. Hori K., Hikage N., Inagaki A., Mori S., Nomura K., Yoshii E. J. Org. Chem. 57:1992;2888-2902
31. Dixon D.J., Ley S.V., Reynolds D.J. Chem. Eur. J. 8:2002;1621-1636
32. Sulfides, sulfoxides and sulfones are known to undergo similar eliminations: Maezaki N., Izumi M., Yuyama S., Sawamoto H., Iwata C., Tanaka T. Tetrahedron. 56:2000;7927-7945
33. Barnes N.J., Davidson A.H., Hughes L.R., Procter G. J. Chem. Soc., Chem. Commun. 1985;1292-1294
34. Caturla F., Nájera C. Tetrahedron. 53:1997;11449-11464
35. Krief A., Kenda B., Remacle B. Tetrahedron. 52:1996;7435-7463
36. 2Bn)
37. Shue Y.-K., Carrera G.M., Tufano M.D., Nadzan A.M. J. Org. Chem. 56:1991;2107-2111
38. tBuOK at -65°C afforded the C-2 epimer of tetrahydrofuran 21
39. Tetronasin (M139603) has a similar structure to 19 but has opposite configurations at the 10 common chiral centres. Hori K., Kazuno H., Nomura K., Yoshii E. Tetrahedron Lett. 34:1993;2183-2186
40. Ley S.V., Brown D.S., Clase J.A., Fairbanks A.J., Lennon I.C., Osborn H.M.I., Stokes (née Owen) E.S.E., Wadsworth D.J. J. Chem. Soc., Perkin Trans. 1. 1998;2259-2276
41. Martinek T., Riddell F.G., Rutherford T.J., Sareth S., Weller C.T. Chem. Commun. 1998;1893-1894