Enantioselective total synthesis of (+)-(2R,6R)-trans-γ-irone

Journal of Organic Chemistry

Volumn 61, Issue 17, 1996, Pages 6021-6023

  Monti, Honoré ^a   Audran, Gérard ^a   Monti, Jean Pierre ^a   Leandri, Gilbert ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CAROTENOID; GAMMA IRONE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029838945     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960392l     Document Type: Article

References (36)

1. Rautenstrauch, V.; Willhalm, B.; Thommen, W.; Ohloff, G. Helv. Chim. Acta 1984, 67, 325.
2. (a) Garnero, J.; Joulain, D. Bull. Soc. Chim. Fr. 1979, 15.
3. (b) Kitahara, T.; Tanida, K.; Mori, K. Agric. Biol. Chem. 1983, 47, 581.
4. (c) Takazawa, O.; Kogami, K.; Hayashi, K. Bull. Chem. Soc. Jpn 1985, 58, 389.
5. (d) Leyendecker, F.; Comte, M.-T. Tetrahedron 1987, 43, 85.
6. Miyashita, M.; Makino, N.; Singh, M.; Yoshikoshi, A. J. Chem. Soc., Perkin Trans, 1 1982, 1303.
7. Helmlinger, D.; Fráter, G. Helv. Chim. Acta 1989, 72, 1515.
8. Audran, G.; Monti, H.; Léandri, G.; Monti, J.-P. Tetrahedron Lett. 1993, 34, 3417.
9. For ene reaction of butynone with alkenes, see: Snider, B. B.; Brown, L. A.; Eichenconn, R. S.; Killinger, T. A. Tetrahedron Lett. 1977, 33, 2831. For closely related electron-deficient alkynes as enophiles, see: (a) Mikami, K.; Loh, T.-P.; Nakai, T. J. Chem. Soc., Chem. Commun. 1988, 1430. (b) Snider, B. B. In Comprehensive Organic Synthesis Vol. 5; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; pp 1-27 and references therein. (c) Dang, H.-S.; Davies, A. G. J. Chem. Soc., Perkin Trans. 2 1991, 721. (d) Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021.
10. For ene reaction of butynone with alkenes, see: Snider, B. B.; Brown, L. A.; Eichenconn, R. S.; Killinger, T. A. Tetrahedron Lett. 1977, 33, 2831. For closely related electron-deficient alkynes as enophiles, see: (a) Mikami, K.; Loh, T.-P.; Nakai, T. J. Chem. Soc., Chem. Commun. 1988, 1430. (b) Snider, B. B. In Comprehensive Organic Synthesis Vol. 5; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; pp 1-27 and references therein. (c) Dang, H.-S.; Davies, A. G. J. Chem. Soc., Perkin Trans. 2 1991, 721. (d) Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021.
11. For ene reaction of butynone with alkenes, see: Snider, B. B.; Brown, L. A.; Eichenconn, R. S.; Killinger, T. A. Tetrahedron Lett. 1977, 33, 2831. For closely related electron-deficient alkynes as enophiles, see: (a) Mikami, K.; Loh, T.-P.; Nakai, T. J. Chem. Soc., Chem. Commun. 1988, 1430. (b) Snider, B. B. In Comprehensive Organic Synthesis Vol. 5; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; pp 1-27 and references therein. (c) Dang, H.-S.; Davies, A. G. J. Chem. Soc., Perkin Trans. 2 1991, 721. (d) Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021.
12. For ene reaction of butynone with alkenes, see: Snider, B. B.; Brown, L. A.; Eichenconn, R. S.; Killinger, T. A. Tetrahedron Lett. 1977, 33, 2831. For closely related electron-deficient alkynes as enophiles, see: (a) Mikami, K.; Loh, T.-P.; Nakai, T. J. Chem. Soc., Chem. Commun. 1988, 1430. (b) Snider, B. B. In Comprehensive Organic Synthesis Vol. 5; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; pp 1-27 and references therein. (c) Dang, H.-S.; Davies, A. G. J. Chem. Soc., Perkin Trans. 2 1991, 721. (d) Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021.
13. For ene reaction of butynone with alkenes, see: Snider, B. B.; Brown, L. A.; Eichenconn, R. S.; Killinger, T. A. Tetrahedron Lett. 1977, 33, 2831. For closely related electron-deficient alkynes as enophiles, see: (a) Mikami, K.; Loh, T.-P.; Nakai, T. J. Chem. Soc., Chem. Commun. 1988, 1430. (b) Snider, B. B. In Comprehensive Organic Synthesis Vol. 5; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; pp 1-27 and references therein. (c) Dang, H.-S.; Davies, A. G. J. Chem. Soc., Perkin Trans. 2 1991, 721. (d) Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021.
14. Thermal ene reactions with allylsilanes. For a review, see: Dubac, J.; Laporterie, A. Chem. Rev. 1987, 87, 319 and references therein. See also: (a) Imazu, S.; Shimizu, N.; Tsuno, Y. Chem. Lett. 1990, 1845. (b) Cai, J.; Davies, A. G. J. Chem. Soc., Perkin Trans. 2 1992, 1743. Lewis acid-promoted ene reactions with allylsilanes: (a) Mikami, K.; Matsukawa, S. Tetrahedron Lett. 1994, 35, 3133. (b) Aoki, S.; Mikami, K.; Terada, M.; Nakai, T. Tetrahedron 1993, 49, 1783.
15. Thermal ene reactions with allylsilanes. For a review, see: Dubac, J.; Laporterie, A. Chem. Rev. 1987, 87, 319 and references therein. See also: (a) Imazu, S.; Shimizu, N.; Tsuno, Y. Chem. Lett. 1990, 1845. (b) Cai, J.; Davies, A. G. J. Chem. Soc., Perkin Trans. 2 1992, 1743. Lewis acid-promoted ene reactions with allylsilanes: (a) Mikami, K.; Matsukawa, S. Tetrahedron Lett. 1994, 35, 3133. (b) Aoki, S.; Mikami, K.; Terada, M.; Nakai, T. Tetrahedron 1993, 49, 1783.
16. Thermal ene reactions with allylsilanes. For a review, see: Dubac, J.; Laporterie, A. Chem. Rev. 1987, 87, 319 and references therein. See also: (a) Imazu, S.; Shimizu, N.; Tsuno, Y. Chem. Lett. 1990, 1845. (b) Cai, J.; Davies, A. G. J. Chem. Soc., Perkin Trans. 2 1992, 1743. Lewis acid-promoted ene reactions with allylsilanes: (a) Mikami, K.; Matsukawa, S. Tetrahedron Lett. 1994, 35, 3133. (b) Aoki, S.; Mikami, K.; Terada, M.; Nakai, T. Tetrahedron 1993, 49, 1783.
17. Thermal ene reactions with allylsilanes. For a review, see: Dubac, J.; Laporterie, A. Chem. Rev. 1987, 87, 319 and references therein. See also: (a) Imazu, S.; Shimizu, N.; Tsuno, Y. Chem. Lett. 1990, 1845. (b) Cai, J.; Davies, A. G. J. Chem. Soc., Perkin Trans. 2 1992, 1743. Lewis acid-promoted ene reactions with allylsilanes: (a) Mikami, K.; Matsukawa, S. Tetrahedron Lett. 1994, 35, 3133. (b) Aoki, S.; Mikami, K.; Terada, M.; Nakai, T. Tetrahedron 1993, 49, 1783.
18. Thermal ene reactions with allylsilanes. For a review, see: Dubac, J.; Laporterie, A. Chem. Rev. 1987, 87, 319 and references therein. See also: (a) Imazu, S.; Shimizu, N.; Tsuno, Y. Chem. Lett. 1990, 1845. (b) Cai, J.; Davies, A. G. J. Chem. Soc., Perkin Trans. 2 1992, 1743. Lewis acid-promoted ene reactions with allylsilanes: (a) Mikami, K.; Matsukawa, S. Tetrahedron Lett. 1994, 35, 3133. (b) Aoki, S.; Mikami, K.; Terada, M.; Nakai, T. Tetrahedron 1993, 49, 1783.
19. 4 led to (+)-(R)-6-methylcyclohex-2-en-1-one (Solladié, G.; Hutt, J. J. Org. Chem. 1987, 52, 3560). (b) Treatment of this ketone with methyllithium, followed by oxidation with pyridinium chlorochromate (PCC), afforded (+)-3 (Iio, H.; Monden, M.; Okada, K.; Tokoroyama, T. J. Chem. Soc., Chem. Commun. 1987, 358. See also: Dauben, W. G.; Michno, D. M. J. Org. Chem. 1977, 42, 682).
20. 4 led to (+)-(R)-6-methylcyclohex-2-en-1-one (Solladié, G.; Hutt, J. J. Org. Chem. 1987, 52, 3560). (b) Treatment of this ketone with methyllithium, followed by oxidation with pyridinium chlorochromate (PCC), afforded (+)-3 (Iio, H.; Monden, M.; Okada, K.; Tokoroyama, T. J. Chem. Soc., Chem. Commun. 1987, 358. See also: Dauben, W. G.; Michno, D. M. J. Org. Chem. 1977, 42, 682).
21. 4 led to (+)-(R)-6-methylcyclohex-2-en-1-one (Solladié, G.; Hutt, J. J. Org. Chem. 1987, 52, 3560). (b) Treatment of this ketone with methyllithium, followed by oxidation with pyridinium chlorochromate (PCC), afforded (+)-3 (Iio, H.; Monden, M.; Okada, K.; Tokoroyama, T. J. Chem. Soc., Chem. Commun. 1987, 358. See also: Dauben, W. G.; Michno, D. M. J. Org. Chem. 1977, 42, 682).
22. (a) Hayashi, T.; Fujiwa, T.; Okamoto, Y.; Katsuro, Y.; Kumada, M. Synthesis 1981, 1001.
23. (b) Danishefsky, S. J.; Mantlo, N. J. Am. Chem. Soc. 1988, 110, 8129.
24. 4
25. (a) Thomas, J. M.; Theocaris, C. R. In Modern Synthetic Methods; Scheffold, R., Ed.; Springer Verlag: Berlin, 1989; p 249.
26. (b) Dyer, A. In An Introduction to Zeolite Molecular Sieves; Wiley: Chichester, 1988.
27. (c) Temme, O.; Laschat, S. J. Chem. Soc., Perkin Trans. 1 1995, 125.
28. Torii, S.; Uneyama, K.; Matsunami, S. J. Org. Chem. 1980, 45, 16.
29. Buchi, G.; Wuest, H. Tetrahedron Lett. 1977, 4305.
30. (a) Snider B. B. Acc. Chem. Res. 1980, 13, 426.
31. (b) Snider, B. B.; Rodini, D. J.; Karras, M.; Kirk, T. C.; Deutsch, E. A.; Cordova, R.; Price, R. T. Tetrahedron 1981, 37, 3927.
32. (c) Snider, B. B.; Rodini, D. J.; Kirk, T. C.; Cordova, R. J. Am. Chem. Soc. 1982, 104, 555.
33. (d) Cartaya-Marin, C. P.; Jackson, A. C.; Snider, B. B. J. Org. Chem. 1984, 49, 2443.
34. (e) Snider, B. B. In Selectivities in Lewis Acid Promoted Reactions; Schinzer, D., Ed.; Fluwer Academic Publishers: London, 1989; p 147.
35. Monti, H.; Feraud, M. Synth. Commun., in press.
36. Prepared like (+)-3 starting from (-)-(2S,5S)-trans-dihydrocarvone (Hua, D. H.; Venkataraman, S. J. Org. Chem. 1988, 53, 1095).