Synthesis of sesquiterpene polyene hydroperoxides by regio- and stereoselective transposition reactions

Tetrahedron

Volumn 54, Issue 42, 1998, Pages 12907-12922

  Fielder, Simon ^a,b   Rowan, Daryl D ^a   Sherburn, Michael S ^c  

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

^b MASSEY UNIVERSITY   (New Zealand)

^c UNIVERSITY OF SYDNEY   (Australia)

Author keywords

Carbonium ions; Peroxides; Polyenes; Regiocontrol

Indexed keywords

HYDROPEROXIDE; POLYENE; SESQUITERPENE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0032532586     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00782-0     Document Type: Article

References (37)

1. 1. Bain, J.M., Mercer, F.V., Aust. J. Biol. Sci., 1963, 16, 442; Meigh, D.F. In The Biochemistry of Fruits and Their Products; Vol. 1; Hulme, A.C., Ed.; Academic: New York, 1970, Ch. 19.
2. 1. Bain, J.M., Mercer, F.V., Aust. J. Biol. Sci., 1963, 16, 442; Meigh, D.F. In The Biochemistry of Fruits and Their Products; Vol. 1; Hulme, A.C., Ed.; Academic: New York, 1970, Ch. 19.
3. 2. Rowan, D.D., Allen, J.M., Fielder, S., Spicer, J.A., Brimble, M.A., J. Agric. Food Chem., 1995, 43, 2040.
4. 3. Anet, E.F.L.J., J. Sci. Food Agric., 1972, 23, 763.
5. 4. Anet, E.F.L.J., Aust. J. Chem., 1969, 22, 2403.
6. 5. Preliminary communication: Fielder, S., Rowan, D.D., Sherburn, M.S., Synlett, 1996, 349.
7. 6. Previously prepared in low yield via non-selective epoxidation of α-farnesene; 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; Brimble, M.A., Rowan, D.D., Spicer, J.A., Aust. J. Chem., 1994, 47, 1979.
8. 6. Previously prepared in low yield via non-selective epoxidation of α-farnesene; 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; Brimble, M.A., Rowan, D.D., Spicer, J.A., Aust. J. Chem., 1994, 47, 1979.
9. 6. Previously prepared in low yield via non-selective epoxidation of α-farnesene; 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; Brimble, M.A., Rowan, D.D., Spicer, J.A., Aust. J. Chem., 1994, 47, 1979.
10. 7. Davies, M.J., Heslin, J.C., Moody, C.J., J. Chem. Soc., Perkin Trans, 1, 1989, 2473.
11. 8. 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.
12. 8. 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. 9. Klusener, P.A.A., Tip, L., Brandsma, L., Tetrahedron, 1991, 47, 2041.
14. 10. Porter, N.A, In Organic Peroxides; Ando, W., Ed.; Wiley: Chichester, 1992; p 101.
15. 11. Boukouvalas, J., Pouliot, R. and Frechette, Y., Tetrahedron Lett., 1995, 36, 4167.
16. 12. 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 (see experimental section).
18. 14. Cori, O., Chayet, L., Perez, L.M., Bunton, C.A., Hachey, D., J. Org. Chem., 1986, 51, 1310.
19. 15. Dewick, P.M., Nat. Prod. Rep., 1997, 14, 111; Croteau, R., Chem. Rev., 1987, 87, 929.
20. 15. Dewick, P.M., Nat. Prod. Rep., 1997, 14, 111; Croteau, R., Chem. Rev., 1987, 87, 929.
21. 16. Cane, D.E., Chem. Rev., 1990, 90, 1089.
22. 3, gave a complex mixture of elimination products, cf. Brimble, M.A., Rowan, D.D., Spicer, J.A., Aust. J. Chem., 1994, 47, 1979;
23. (b) alcohol (18): Hengartner, U., Bernhard, K., Meyer, K., Englert, G., Glinz, E., Helv. Chim. Acta, 1992, 75, 1848;
24. (c) alcohol (20): Clough, J.M., Pattenden, G., Tetrahedron, 1981, 37, 3911.
25. 18. For (18)→(3), temperature, time for complete reaction, 3E:3Z ratio: -10°C, 48h, 77:23; 60°C, 1h, 71:29.
26. 19. Hoffmann, H.M.R., Angew. Chem., Int. Ed. Engl., 1973, 12, 819; Bollinger, J.M., Brinich, J.M., Olah, G.A., J. Am. Chem. Soc., 1970, 92, 4025
27. 19. Hoffmann, H.M.R., Angew. Chem., Int. Ed. Engl., 1973, 12, 819; Bollinger, J.M., Brinich, J.M., Olah, G.A., J. Am. Chem. Soc., 1970, 92, 4025
28. 20. Corey, E.J., Wang, Z. Tetrahedron Lett., 1994, 35, 539.
29. 21. Low levels of diastereoselection for cyclisations of this type have been noted previously: Porter, N.A., Zuraw, P.J., J. Org. Chem., 1984, 49, 1345 and references therein.
30. 22. For palladium-catalysed rearrangement of allylic acetates to give conjugated trienyl acetates, see Mladenova, M., Alarm, M, Linstrumelle, G., Tetrahedron Lett., 1996, 37, 6547.
31. 3-catalysed rearrangements of allylic methoxyacetates see Shull, B.K.; Sakai, T., Koreeda, M., J. Am. Chem. Soc., 1996, 118, 11690.
32. 24. Mineral acid-catalysed transpositions of allylic alcohols are well known: see Braude, E.A., Quart. Rev. Chem. Soc., 1950, 4, 404. For recent synthetic applications see Dai, W.-M., Fong, K.C., Tetrahedron Lett., 1996, 37, 8413; Westermann, B., Dubberke, S., Liebigs Ann./Recueil, 1997, 375.
33. 24. Mineral acid-catalysed transpositions of allylic alcohols are well known: see Braude, E.A., Quart. Rev. Chem. Soc., 1950, 4, 404. For recent synthetic applications see Dai, W.-M., Fong, K.C., Tetrahedron Lett., 1996, 37, 8413; Westermann, B., Dubberke, S., Liebigs Ann./Recueil, 1997, 375.
34. 24. Mineral acid-catalysed transpositions of allylic alcohols are well known: see Braude, E.A., Quart. Rev. Chem. Soc., 1950, 4, 404. For recent synthetic applications see Dai, W.-M., Fong, K.C., Tetrahedron Lett., 1996, 37, 8413; Westermann, B., Dubberke, S., Liebigs Ann./Recueil, 1997, 375.
35. 25. Sharpless, K.B., Michaelson, R.C., J. Am. Chem. Soc., 1973, 95, 6136.
36. 26. Lange, G.L., Gottardo, C., Synth. Commun., 1990, 20, 1473.
37. 2 gave higher yields than the reported procedure: Russell, A., Kenyon, R.L., Org. Synth. Coll. Vol. 3, 747.