Patchouli fragrance chemistry : Stereoselective synthesis of (±)-iso-norpatchoulenol

Synthetic Communications

Volumn 26, Issue 22, 1996, Pages 4123-4130

  Monti, Honoré ^a   Charles, Patrick ^a   Léandri, Gilbert ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0007363494     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919608004649     Document Type: Article

References (32)

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15. Trost, B. M.; Verhoeven, T. R. J. Am. Chem. Soc. 1980, 102, 4743.
16. Schlosser, M. Topics Stereochem. 1970, 5, 1. Majoritary (Z)-bromoalkenes : (a) Matsumoto, M.; Kuroda, K. Tetrahedron Lett. 1980, 21, 4021. (b) Avignon-Tropis, M.; Berjeaud, J. M.; Pougny J. R.; Frechard-Ortuno, I.; Guillerm, D.; Linstrumelle, G. J. Org. Chem. 1992, 57, 651. (Z)-1-iodo-1-alkenes : Stork, G.; Zhao, K. Tetrahedron Lett. 1989, 30, 2173.
17. Schlosser, M. Topics Stereochem. 1970, 5, 1. Majoritary (Z)-bromoalkenes : (a) Matsumoto, M.; Kuroda, K. Tetrahedron Lett. 1980, 21, 4021. (b) Avignon-Tropis, M.; Berjeaud, J. M.; Pougny J. R.; Frechard-Ortuno, I.; Guillerm, D.; Linstrumelle, G. J. Org. Chem. 1992, 57, 651. (Z)-1-iodo-1-alkenes : Stork, G.; Zhao, K. Tetrahedron Lett. 1989, 30, 2173.
18. Schlosser, M. Topics Stereochem. 1970, 5, 1. Majoritary (Z)-bromoalkenes : (a) Matsumoto, M.; Kuroda, K. Tetrahedron Lett. 1980, 21, 4021. (b) Avignon-Tropis, M.; Berjeaud, J. M.; Pougny J. R.; Frechard-Ortuno, I.; Guillerm, D.; Linstrumelle, G. J. Org. Chem. 1992, 57, 651. (Z)-1-iodo-1-alkenes : Stork, G.; Zhao, K. Tetrahedron Lett. 1989, 30, 2173.
19. Schlosser, M. Topics Stereochem. 1970, 5, 1. Majoritary (Z)-bromoalkenes : (a) Matsumoto, M.; Kuroda, K. Tetrahedron Lett. 1980, 21, 4021. (b) Avignon-Tropis, M.; Berjeaud, J. M.; Pougny J. R.; Frechard-Ortuno, I.; Guillerm, D.; Linstrumelle, G. J. Org. Chem. 1992, 57, 651. (Z)-1-iodo-1-alkenes : Stork, G.; Zhao, K. Tetrahedron Lett. 1989, 30, 2173.
20. Zhang, X.-p.; Schlosser, M. Tetrahedron Lett. 1993, 34, 1925.
21. The authors thank Prof. M. Schlosser for personnal communication about the synthesis of bromomethyl tris(2-methoxymethoxyphenyl) phosphonium iodide starting from tris(2-methoxymethoxyphenyl) phosphine (Jeganathan, S.; Tsukamoto, M.; Schlosser, M. Synthesis 1990, 109) and bromoiodomethane (Lee, S. J.; Bersohn, R. J. Phys. Chem. 1982, 86, 728).
22. The authors thank Prof. M. Schlosser for personnal communication about the synthesis of bromomethyl tris(2-methoxymethoxyphenyl) phosphonium iodide starting from tris(2-methoxymethoxyphenyl) phosphine (Jeganathan, S.; Tsukamoto, M.; Schlosser, M. Synthesis 1990, 109) and bromoiodomethane (Lee, S. J.; Bersohn, R. J. Phys. Chem. 1982, 86, 728).
23. In this sequence, the second equiv of ter-butyllithium rapidly reacts with the ter-butyl bromide formed to give the innocuous by-products isobutene and lithium halide and avoids side reactions.
24. Alkenyllithiums by lithium-halogen exchange : (a) Cahiez, G.; Bernard, D.; Normant, J. F. Synthesis 1976, 245. (b) Neumann, H.; Seebach, D. Chem. Ber. 1978, 111, 2785. (c) Walborsky, H. M.; Banks, R. B. Bull. Soc. Chim. Belg. 1980, 89, 849. (d) Walborsky, H. M.; Banks, R. B.; Banks, M. L. A.; Duraisamy, M. Organometallics 1982, 1, 667. (e) Duraisamy, M.; Walborsky, H. M. J. Am. Chem. Soc. 1983, 105, 3252. (f) Lee, S. H.; Schartz, J. J. Am. Chem. Soc. 1986, 108, 2445. (g) Bailey, W. F.; Patricia, J. J. J. Organomet. Chem. 1988, 352, 1 and references cited therein. (h) Yokoo, T.; Shinokubo, H.; Oshima, K.; Utimoto, K. Synlett 1994, 645. (i) Bachki, A.; Foubelo, F.; Yus, M. Tetrahedron Lett. 1994, 35, 7643.
25. Alkenyllithiums by lithium-halogen exchange : (a) Cahiez, G.; Bernard, D.; Normant, J. F. Synthesis 1976, 245. (b) Neumann, H.; Seebach, D. Chem. Ber. 1978, 111, 2785. (c) Walborsky, H. M.; Banks, R. B. Bull. Soc. Chim. Belg. 1980, 89, 849. (d) Walborsky, H. M.; Banks, R. B.; Banks, M. L. A.; Duraisamy, M. Organometallics 1982, 1, 667. (e) Duraisamy, M.; Walborsky, H. M. J. Am. Chem. Soc. 1983, 105, 3252. (f) Lee, S. H.; Schartz, J. J. Am. Chem. Soc. 1986, 108, 2445. (g) Bailey, W. F.; Patricia, J. J. J. Organomet. Chem. 1988, 352, 1 and references cited therein. (h) Yokoo, T.; Shinokubo, H.; Oshima, K.; Utimoto, K. Synlett 1994, 645. (i) Bachki, A.; Foubelo, F.; Yus, M. Tetrahedron Lett. 1994, 35, 7643.
26. Alkenyllithiums by lithium-halogen exchange : (a) Cahiez, G.; Bernard, D.; Normant, J. F. Synthesis 1976, 245. (b) Neumann, H.; Seebach, D. Chem. Ber. 1978, 111, 2785. (c) Walborsky, H. M.; Banks, R. B. Bull. Soc. Chim. Belg. 1980, 89, 849. (d) Walborsky, H. M.; Banks, R. B.; Banks, M. L. A.; Duraisamy, M. Organometallics 1982, 1, 667. (e) Duraisamy, M.; Walborsky, H. M. J. Am. Chem. Soc. 1983, 105, 3252. (f) Lee, S. H.; Schartz, J. J. Am. Chem. Soc. 1986, 108, 2445. (g) Bailey, W. F.; Patricia, J. J. J. Organomet. Chem. 1988, 352, 1 and references cited therein. (h) Yokoo, T.; Shinokubo, H.; Oshima, K.; Utimoto, K. Synlett 1994, 645. (i) Bachki, A.; Foubelo, F.; Yus, M. Tetrahedron Lett. 1994, 35, 7643.
27. Alkenyllithiums by lithium-halogen exchange : (a) Cahiez, G.; Bernard, D.; Normant, J. F. Synthesis 1976, 245. (b) Neumann, H.; Seebach, D. Chem. Ber. 1978, 111, 2785. (c) Walborsky, H. M.; Banks, R. B. Bull. Soc. Chim. Belg. 1980, 89, 849. (d) Walborsky, H. M.; Banks, R. B.; Banks, M. L. A.; Duraisamy, M. Organometallics 1982, 1, 667. (e) Duraisamy, M.; Walborsky, H. M. J. Am. Chem. Soc. 1983, 105, 3252. (f) Lee, S. H.; Schartz, J. J. Am. Chem. Soc. 1986, 108, 2445. (g) Bailey, W. F.; Patricia, J. J. J. Organomet. Chem. 1988, 352, 1 and references cited therein. (h) Yokoo, T.; Shinokubo, H.; Oshima, K.; Utimoto, K. Synlett 1994, 645. (i) Bachki, A.; Foubelo, F.; Yus, M. Tetrahedron Lett. 1994, 35, 7643.
28. Alkenyllithiums by lithium-halogen exchange : (a) Cahiez, G.; Bernard, D.; Normant, J. F. Synthesis 1976, 245. (b) Neumann, H.; Seebach, D. Chem. Ber. 1978, 111, 2785. (c) Walborsky, H. M.; Banks, R. B. Bull. Soc. Chim. Belg. 1980, 89, 849. (d) Walborsky, H. M.; Banks, R. B.; Banks, M. L. A.; Duraisamy, M. Organometallics 1982, 1, 667. (e) Duraisamy, M.; Walborsky, H. M. J. Am. Chem. Soc. 1983, 105, 3252. (f) Lee, S. H.; Schartz, J. J. Am. Chem. Soc. 1986, 108, 2445. (g) Bailey, W. F.; Patricia, J. J. J. Organomet. Chem. 1988, 352, 1 and references cited therein. (h) Yokoo, T.; Shinokubo, H.; Oshima, K.; Utimoto, K. Synlett 1994, 645. (i) Bachki, A.; Foubelo, F.; Yus, M. Tetrahedron Lett. 1994, 35, 7643.
29. Alkenyllithiums by lithium-halogen exchange : (a) Cahiez, G.; Bernard, D.; Normant, J. F. Synthesis 1976, 245. (b) Neumann, H.; Seebach, D. Chem. Ber. 1978, 111, 2785. (c) Walborsky, H. M.; Banks, R. B. Bull. Soc. Chim. Belg. 1980, 89, 849. (d) Walborsky, H. M.; Banks, R. B.; Banks, M. L. A.; Duraisamy, M. Organometallics 1982, 1, 667. (e) Duraisamy, M.; Walborsky, H. M. J. Am. Chem. Soc. 1983, 105, 3252. (f) Lee, S. H.; Schartz, J. J. Am. Chem. Soc. 1986, 108, 2445. (g) Bailey, W. F.; Patricia, J. J. J. Organomet. Chem. 1988, 352, 1 and references cited therein. (h) Yokoo, T.; Shinokubo, H.; Oshima, K.; Utimoto, K. Synlett 1994, 645. (i) Bachki, A.; Foubelo, F.; Yus, M. Tetrahedron Lett. 1994, 35, 7643.
30. Alkenyllithiums by lithium-halogen exchange : (a) Cahiez, G.; Bernard, D.; Normant, J. F. Synthesis 1976, 245. (b) Neumann, H.; Seebach, D. Chem. Ber. 1978, 111, 2785. (c) Walborsky, H. M.; Banks, R. B. Bull. Soc. Chim. Belg. 1980, 89, 849. (d) Walborsky, H. M.; Banks, R. B.; Banks, M. L. A.; Duraisamy, M. Organometallics 1982, 1, 667. (e) Duraisamy, M.; Walborsky, H. M. J. Am. Chem. Soc. 1983, 105, 3252. (f) Lee, S. H.; Schartz, J. J. Am. Chem. Soc. 1986, 108, 2445. (g) Bailey, W. F.; Patricia, J. J. J. Organomet. Chem. 1988, 352, 1 and references cited therein. (h) Yokoo, T.; Shinokubo, H.; Oshima, K.; Utimoto, K. Synlett 1994, 645. (i) Bachki, A.; Foubelo, F.; Yus, M. Tetrahedron Lett. 1994, 35, 7643.
31. Alkenyllithiums by lithium-halogen exchange : (a) Cahiez, G.; Bernard, D.; Normant, J. F. Synthesis 1976, 245. (b) Neumann, H.; Seebach, D. Chem. Ber. 1978, 111, 2785. (c) Walborsky, H. M.; Banks, R. B. Bull. Soc. Chim. Belg. 1980, 89, 849. (d) Walborsky, H. M.; Banks, R. B.; Banks, M. L. A.; Duraisamy, M. Organometallics 1982, 1, 667. (e) Duraisamy, M.; Walborsky, H. M. J. Am. Chem. Soc. 1983, 105, 3252. (f) Lee, S. H.; Schartz, J. J. Am. Chem. Soc. 1986, 108, 2445. (g) Bailey, W. F.; Patricia, J. J. J. Organomet. Chem. 1988, 352, 1 and references cited therein. (h) Yokoo, T.; Shinokubo, H.; Oshima, K.; Utimoto, K. Synlett 1994, 645. (i) Bachki, A.; Foubelo, F.; Yus, M. Tetrahedron Lett. 1994, 35, 7643.
32. Alkenyllithiums by lithium-halogen exchange : (a) Cahiez, G.; Bernard, D.; Normant, J. F. Synthesis 1976, 245. (b) Neumann, H.; Seebach, D. Chem. Ber. 1978, 111, 2785. (c) Walborsky, H. M.; Banks, R. B. Bull. Soc. Chim. Belg. 1980, 89, 849. (d) Walborsky, H. M.; Banks, R. B.; Banks, M. L. A.; Duraisamy, M. Organometallics 1982, 1, 667. (e) Duraisamy, M.; Walborsky, H. M. J. Am. Chem. Soc. 1983, 105, 3252. (f) Lee, S. H.; Schartz, J. J. Am. Chem. Soc. 1986, 108, 2445. (g) Bailey, W. F.; Patricia, J. J. J. Organomet. Chem. 1988, 352, 1 and references cited therein. (h) Yokoo, T.; Shinokubo, H.; Oshima, K.; Utimoto, K. Synlett 1994, 645. (i) Bachki, A.; Foubelo, F.; Yus, M. Tetrahedron Lett. 1994, 35, 7643.