Synthesis of α-Farnesene Hydroperoxides

Synlett

Volumn 1996, Issue 4, 1996, Pages 349-350

  Fielder, Simon ^a   Rowand, Daryl D ^a   Sherburn, Michael S ^b  

^a THE NEW ZEALAND INSTITUTE FOR PLANT AND FOOD RESEARCH LIMITED   (New Zealand)

^b MASSEY UNIVERSITY   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000251008     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5421     Document Type: Article

References (21)

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2. Meigh, D.F. In The Biochemistry of Fruits and Their Products; Vol. 1; Hulme, A.C., Ed.; Academic: New York, 1970, Ch. 19.
3. Anet, E.F.L.J., J. Sci. Food Agric., 1972, 23, 763.
4. Anet, E.F.L.J., Aust. J. Chem., 1969, 22, 2403.
5. Rowan, D.D., Allen, J.M., Fielder, S., Spicer, J.A., Brimble, M.A., J. Agric. Food Chem., 1995, 43, 2040.
6. Epoxidation of α-farnesene is poorly regioselective; see Spicer, J.A., Brimble, M.A., Rowan, D.D., Aust. J. Chem., 1993, 46, 1929; Fielder, S., Rowan, D.D., J. Labelled Compd. Radiopharm., 1994, 34, 1075.
7. Epoxidation of α-farnesene is poorly regioselective; see Spicer, J.A., Brimble, M.A., Rowan, D.D., Aust. J. Chem., 1993, 46, 1929; Fielder, S., Rowan, D.D., J. Labelled Compd. Radiopharm., 1994, 34, 1075.
8. Brimble, M.A., Rowan, D.D., Spicer, J.A., Aust, J. Chem., 1994, 47, 1979.
9. Sharpless, K.B., Michaelson, R.C., J. Am. Chem. Soc., 1973, 95, 6136.
10. 13C NMR, IR, UV and high resolution MS.
11. Lange, G.L., Gottardo, C., Synth. Commun., 1990, 20, 1473.
12. Chou, T., Tso, H., Chang, L., J. Chem. Soc., Chem. Commun., 1984, 1323; Fielder, S., Rowan, D.D., Reay, P.F., J. Labelled Compd. Radiopharm., 1993, 33, 965.
13. Chou, T., Tso, H., Chang, L., J. Chem. Soc., Chem. Commun., 1984, 1323; Fielder, S., Rowan, D.D., Reay, P.F., J. Labelled Compd. Radiopharm., 1993, 33, 965.
14. Porter, N.A, In Organic Peroxides; Ando, W., Ed.; Wiley: Chichester, 1992; p 101.
15. Boukouvalas, J., Pouliot, R. and Frechette, Y., Tetrahedron Lett., 1995, 36, 4167.
16. Rocha Gonsalves, A.M.d'A., Johnstone, R.A.W., Pereira, M.M., Shaw, J., J. Chem. Res. (S), 1991, 208.
17. 2, hydroperoxides and endoperoxides.
18. 2 requires 236.1776), 218(8), 202(9), 162(34), 159(34), 137(29), 119(31), 105(42), 93(55), 81(35), 69(89), 55(52), 43(100), 41(85).
19. Corey, E.J., Wang, Z. Tetrahedron Lett., 1994, 35, 539.
20. Porter, N.A., Zuraw, P.J., J. Org. Chem., 1984, 49, 1345 and references therein.
21. 17 Preliminary investigations indicate that samarium (III) iodide and oxygen can also initiate this type of reaction, albeit less efficiently than 'oxidised' samarium (II) iodide. A future report from these laboratories will document the relative merits of each system.