Enzymatic desymmetrization of meso-2,6-dimethyl-1,7-heptanediol. Enantioselective formal synthesis of the vitamin E side chain and the insect pheromone tribolure

Journal of Organic Chemistry

Volumn 61, Issue 4, 1996, Pages 1219-1220

  Chênevert, Robert ^a   Desjardins, Michel ^a  

^a UNIVERSITÉ LAVAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA TOCOPHEROL DERIVATIVE; PHEROMONE; TRIBOLURE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS;

EID: 0029868182     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9516650     Document Type: Article

References (45)

1. Mercier, C.; Chabardes, P. Pure Appl. Chem. 1994, 66, 1509.
2. Dowd, P.; Hershline, R.; Ham, S. W.; Naganathan, S. Nat. Prod. Rep. 1994, 11, 251.
3. Connolly, J. D.; Hill, R. A. Dictionary of Terpenoids: Vol. 2, Di-and higher terpenoids; Chapman and Hall: London, 1991.
4. Brown, G. D. Phytochemistry 1994, 36, 1553.
5. (a) Aldrich, J. R.; Oliver, J. E.; Lusby, W. R.; Kochansky, J. P.; Borges, M. J. Chem. Ecol. 1994, 20, 1103.
6. (b) Mori, K. Tetrahedron 1989, 45, 3233.
7. Mori, K. The Synthesis of Insect Pheromones. In The Total Synthesis of Natural Products; ApSimon, Ed.; Wiley: 1992; Vol. 9.
8. Minale, L. Terpenoids from Marine Sponges. In Marine Natural Products; Scheuer, P. J., Ed.; Academic Press: 1978; Vol. 1, Chapter 4.
9. Zhang, D.; Poulter, C. D. J. Am. Chem. Soc. 1993, 115, 1270.
10. Still, W. C.; Darst, K. P. J. Am. Chem. Soc. 1980, 102, 7385.
11. For other examples, see: 9 (a) Wallace, T. S.; Baldwin, G. W.; Morrow, C. J. J. Org. Chem. 1992, 57, 5231. (b) Takemura, T.; Saito, K.; Nakazawa, S.; Mori, N. Tetrahedron Lett. 1992, 33, 6335. (c) Caron, G.; Kazlauskas, R. J. Tetrahedron: Asymmetry 1994, 5, 657.
12. For other examples, see: 9 (a) Wallace, T. S.; Baldwin, G. W.; Morrow, C. J. J. Org. Chem. 1992, 57, 5231. (b) Takemura, T.; Saito, K.; Nakazawa, S.; Mori, N. Tetrahedron Lett. 1992, 33, 6335. (c) Caron, G.; Kazlauskas, R. J. Tetrahedron: Asymmetry 1994, 5, 657.
13. For other examples, see: 9 (a) Wallace, T. S.; Baldwin, G. W.; Morrow, C. J. J. Org. Chem. 1992, 57, 5231. (b) Takemura, T.; Saito, K.; Nakazawa, S.; Mori, N. Tetrahedron Lett. 1992, 33, 6335. (c) Caron, G.; Kazlauskas, R. J. Tetrahedron: Asymmetry 1994, 5, 657.
14. Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936.
15. 14 side chain: (a) Scott, J. W.; Bizzaro, F. T.; Parrish, D. R.; Saucy, G. Helv. Chim. Acta 1976, 59, 290. (b) Cohen, N.; Eichel, W. F.; Lopresh, R. J.; Neukom, C.; Saucy, G. J. Org. Chem. 1976, 41, 3505. (c) Fuganti, C.; Grasselli, P. J. Chem. Soc., Chem. Commun. 1979, 995. (d) Heathcock, C. H.; Jarvi, E. T. Tetrahedron Lett. 1982, 23, 2825. (e) Helmchen, G.; Schmierer, R. Tetrahedron Lett. 1983, 24, 1235. (f) Bérubé, G.; Deslongchamps P. Can. J. Chem. 1984, 62, 1558. (g) Bérubé, G.; Deslongchamps, P. Bull. Soc. Chim. Fr. 1987, 103. (h) Takano, S.; Shimazaki, Y.; Iwahushi, Y.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 3619. (i) Naoshima, Y.; Munakata, Y.; Yoshida, S.; Funai, A. J. Chem. Soc. Perkin Trans. 1 1991, 549. (j) Mori, K.; Harada, H.; Zagatti, P.; Cork, A.; Hall, D. R Liebigs Ann. Chem. 1991, 259. (k) Takabe, K; Sawada, H.; Satani, T.; Yamada, T.; Katagiri, T.; Yoda, H. Rioorg. Med. Chem. Lett. 1993, 3, 157. (l) Molander, G. A.; Shakya, S. R. J. Org. Chem. 1994, 59, 3445.
16. 14 side chain: (a) Scott, J. W.; Bizzaro, F. T.; Parrish, D. R.; Saucy, G. Helv. Chim. Acta 1976, 59, 290. (b) Cohen, N.; Eichel, W. F.; Lopresh, R. J.; Neukom, C.; Saucy, G. J. Org. Chem. 1976, 41, 3505. (c) Fuganti, C.; Grasselli, P. J. Chem. Soc., Chem. Commun. 1979, 995. (d) Heathcock, C. H.; Jarvi, E. T. Tetrahedron Lett. 1982, 23, 2825. (e) Helmchen, G.; Schmierer, R. Tetrahedron Lett. 1983, 24, 1235. (f) Bérubé, G.; Deslongchamps P. Can. J. Chem. 1984, 62, 1558. (g) Bérubé, G.; Deslongchamps, P. Bull. Soc. Chim. Fr. 1987, 103. (h) Takano, S.; Shimazaki, Y.; Iwahushi, Y.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 3619. (i) Naoshima, Y.; Munakata, Y.; Yoshida, S.; Funai, A. J. Chem. Soc. Perkin Trans. 1 1991, 549. (j) Mori, K.; Harada, H.; Zagatti, P.; Cork, A.; Hall, D. R Liebigs Ann. Chem. 1991, 259. (k) Takabe, K; Sawada, H.; Satani, T.; Yamada, T.; Katagiri, T.; Yoda, H. Rioorg. Med. Chem. Lett. 1993, 3, 157. (l) Molander, G. A.; Shakya, S. R. J. Org. Chem. 1994, 59, 3445.
17. 14 side chain: (a) Scott, J. W.; Bizzaro, F. T.; Parrish, D. R.; Saucy, G. Helv. Chim. Acta 1976, 59, 290. (b) Cohen, N.; Eichel, W. F.; Lopresh, R. J.; Neukom, C.; Saucy, G. J. Org. Chem. 1976, 41, 3505. (c) Fuganti, C.; Grasselli, P. J. Chem. Soc., Chem. Commun. 1979, 995. (d) Heathcock, C. H.; Jarvi, E. T. Tetrahedron Lett. 1982, 23, 2825. (e) Helmchen, G.; Schmierer, R. Tetrahedron Lett. 1983, 24, 1235. (f) Bérubé, G.; Deslongchamps P. Can. J. Chem. 1984, 62, 1558. (g) Bérubé, G.; Deslongchamps, P. Bull. Soc. Chim. Fr. 1987, 103. (h) Takano, S.; Shimazaki, Y.; Iwahushi, Y.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 3619. (i) Naoshima, Y.; Munakata, Y.; Yoshida, S.; Funai, A. J. Chem. Soc. Perkin Trans. 1 1991, 549. (j) Mori, K.; Harada, H.; Zagatti, P.; Cork, A.; Hall, D. R Liebigs Ann. Chem. 1991, 259. (k) Takabe, K; Sawada, H.; Satani, T.; Yamada, T.; Katagiri, T.; Yoda, H. Rioorg. Med. Chem. Lett. 1993, 3, 157. (l) Molander, G. A.; Shakya, S. R. J. Org. Chem. 1994, 59, 3445.
18. 14 side chain: (a) Scott, J. W.; Bizzaro, F. T.; Parrish, D. R.; Saucy, G. Helv. Chim. Acta 1976, 59, 290. (b) Cohen, N.; Eichel, W. F.; Lopresh, R. J.; Neukom, C.; Saucy, G. J. Org. Chem. 1976, 41, 3505. (c) Fuganti, C.; Grasselli, P. J. Chem. Soc., Chem. Commun. 1979, 995. (d) Heathcock, C. H.; Jarvi, E. T. Tetrahedron Lett. 1982, 23, 2825. (e) Helmchen, G.; Schmierer, R. Tetrahedron Lett. 1983, 24, 1235. (f) Bérubé, G.; Deslongchamps P. Can. J. Chem. 1984, 62, 1558. (g) Bérubé, G.; Deslongchamps, P. Bull. Soc. Chim. Fr. 1987, 103. (h) Takano, S.; Shimazaki, Y.; Iwahushi, Y.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 3619. (i) Naoshima, Y.; Munakata, Y.; Yoshida, S.; Funai, A. J. Chem. Soc. Perkin Trans. 1 1991, 549. (j) Mori, K.; Harada, H.; Zagatti, P.; Cork, A.; Hall, D. R Liebigs Ann. Chem. 1991, 259. (k) Takabe, K; Sawada, H.; Satani, T.; Yamada, T.; Katagiri, T.; Yoda, H. Rioorg. Med. Chem. Lett. 1993, 3, 157. (l) Molander, G. A.; Shakya, S. R. J. Org. Chem. 1994, 59, 3445.
19. 14 side chain: (a) Scott, J. W.; Bizzaro, F. T.; Parrish, D. R.; Saucy, G. Helv. Chim. Acta 1976, 59, 290. (b) Cohen, N.; Eichel, W. F.; Lopresh, R. J.; Neukom, C.; Saucy, G. J. Org. Chem. 1976, 41, 3505. (c) Fuganti, C.; Grasselli, P. J. Chem. Soc., Chem. Commun. 1979, 995. (d) Heathcock, C. H.; Jarvi, E. T. Tetrahedron Lett. 1982, 23, 2825. (e) Helmchen, G.; Schmierer, R. Tetrahedron Lett. 1983, 24, 1235. (f) Bérubé, G.; Deslongchamps P. Can. J. Chem. 1984, 62, 1558. (g) Bérubé, G.; Deslongchamps, P. Bull. Soc. Chim. Fr. 1987, 103. (h) Takano, S.; Shimazaki, Y.; Iwahushi, Y.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 3619. (i) Naoshima, Y.; Munakata, Y.; Yoshida, S.; Funai, A. J. Chem. Soc. Perkin Trans. 1 1991, 549. (j) Mori, K.; Harada, H.; Zagatti, P.; Cork, A.; Hall, D. R Liebigs Ann. Chem. 1991, 259. (k) Takabe, K; Sawada, H.; Satani, T.; Yamada, T.; Katagiri, T.; Yoda, H. Rioorg. Med. Chem. Lett. 1993, 3, 157. (l) Molander, G. A.; Shakya, S. R. J. Org. Chem. 1994, 59, 3445.
20. 14 side chain: (a) Scott, J. W.; Bizzaro, F. T.; Parrish, D. R.; Saucy, G. Helv. Chim. Acta 1976, 59, 290. (b) Cohen, N.; Eichel, W. F.; Lopresh, R. J.; Neukom, C.; Saucy, G. J. Org. Chem. 1976, 41, 3505. (c) Fuganti, C.; Grasselli, P. J. Chem. Soc., Chem. Commun. 1979, 995. (d) Heathcock, C. H.; Jarvi, E. T. Tetrahedron Lett. 1982, 23, 2825. (e) Helmchen, G.; Schmierer, R. Tetrahedron Lett. 1983, 24, 1235. (f) Bérubé, G.; Deslongchamps P. Can. J. Chem. 1984, 62, 1558. (g) Bérubé, G.; Deslongchamps, P. Bull. Soc. Chim. Fr. 1987, 103. (h) Takano, S.; Shimazaki, Y.; Iwahushi, Y.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 3619. (i) Naoshima, Y.; Munakata, Y.; Yoshida, S.; Funai, A. J. Chem. Soc. Perkin Trans. 1 1991, 549. (j) Mori, K.; Harada, H.; Zagatti, P.; Cork, A.; Hall, D. R Liebigs Ann. Chem. 1991, 259. (k) Takabe, K; Sawada, H.; Satani, T.; Yamada, T.; Katagiri, T.; Yoda, H. Rioorg. Med. Chem. Lett. 1993, 3, 157. (l) Molander, G. A.; Shakya, S. R. J. Org. Chem. 1994, 59, 3445.
21. 14 side chain: (a) Scott, J. W.; Bizzaro, F. T.; Parrish, D. R.; Saucy, G. Helv. Chim. Acta 1976, 59, 290. (b) Cohen, N.; Eichel, W. F.; Lopresh, R. J.; Neukom, C.; Saucy, G. J. Org. Chem. 1976, 41, 3505. (c) Fuganti, C.; Grasselli, P. J. Chem. Soc., Chem. Commun. 1979, 995. (d) Heathcock, C. H.; Jarvi, E. T. Tetrahedron Lett. 1982, 23, 2825. (e) Helmchen, G.; Schmierer, R. Tetrahedron Lett. 1983, 24, 1235. (f) Bérubé, G.; Deslongchamps P. Can. J. Chem. 1984, 62, 1558. (g) Bérubé, G.; Deslongchamps, P. Bull. Soc. Chim. Fr. 1987, 103. (h) Takano, S.; Shimazaki, Y.; Iwahushi, Y.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 3619. (i) Naoshima, Y.; Munakata, Y.; Yoshida, S.; Funai, A. J. Chem. Soc. Perkin Trans. 1 1991, 549. (j) Mori, K.; Harada, H.; Zagatti, P.; Cork, A.; Hall, D. R Liebigs Ann. Chem. 1991, 259. (k) Takabe, K; Sawada, H.; Satani, T.; Yamada, T.; Katagiri, T.; Yoda, H. Rioorg. Med. Chem. Lett. 1993, 3, 157. (l) Molander, G. A.; Shakya, S. R. J. Org. Chem. 1994, 59, 3445.
22. 14 side chain: (a) Scott, J. W.; Bizzaro, F. T.; Parrish, D. R.; Saucy, G. Helv. Chim. Acta 1976, 59, 290. (b) Cohen, N.; Eichel, W. F.; Lopresh, R. J.; Neukom, C.; Saucy, G. J. Org. Chem. 1976, 41, 3505. (c) Fuganti, C.; Grasselli, P. J. Chem. Soc., Chem. Commun. 1979, 995. (d) Heathcock, C. H.; Jarvi, E. T. Tetrahedron Lett. 1982, 23, 2825. (e) Helmchen, G.; Schmierer, R. Tetrahedron Lett. 1983, 24, 1235. (f) Bérubé, G.; Deslongchamps P. Can. J. Chem. 1984, 62, 1558. (g) Bérubé, G.; Deslongchamps, P. Bull. Soc. Chim. Fr. 1987, 103. (h) Takano, S.; Shimazaki, Y.; Iwahushi, Y.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 3619. (i) Naoshima, Y.; Munakata, Y.; Yoshida, S.; Funai, A. J. Chem. Soc. Perkin Trans. 1 1991, 549. (j) Mori, K.; Harada, H.; Zagatti, P.; Cork, A.; Hall, D. R Liebigs Ann. Chem. 1991, 259. (k) Takabe, K; Sawada, H.; Satani, T.; Yamada, T.; Katagiri, T.; Yoda, H. Rioorg. Med. Chem. Lett. 1993, 3, 157. (l) Molander, G. A.; Shakya, S. R. J. Org. Chem. 1994, 59, 3445.
23. 14 side chain: (a) Scott, J. W.; Bizzaro, F. T.; Parrish, D. R.; Saucy, G. Helv. Chim. Acta 1976, 59, 290. (b) Cohen, N.; Eichel, W. F.; Lopresh, R. J.; Neukom, C.; Saucy, G. J. Org. Chem. 1976, 41, 3505. (c) Fuganti, C.; Grasselli, P. J. Chem. Soc., Chem. Commun. 1979, 995. (d) Heathcock, C. H.; Jarvi, E. T. Tetrahedron Lett. 1982, 23, 2825. (e) Helmchen, G.; Schmierer, R. Tetrahedron Lett. 1983, 24, 1235. (f) Bérubé, G.; Deslongchamps P. Can. J. Chem. 1984, 62, 1558. (g) Bérubé, G.; Deslongchamps, P. Bull. Soc. Chim. Fr. 1987, 103. (h) Takano, S.; Shimazaki, Y.; Iwahushi, Y.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 3619. (i) Naoshima, Y.; Munakata, Y.; Yoshida, S.; Funai, A. J. Chem. Soc. Perkin Trans. 1 1991, 549. (j) Mori, K.; Harada, H.; Zagatti, P.; Cork, A.; Hall, D. R Liebigs Ann. Chem. 1991, 259. (k) Takabe, K; Sawada, H.; Satani, T.; Yamada, T.; Katagiri, T.; Yoda, H. Rioorg. Med. Chem. Lett. 1993, 3, 157. (l) Molander, G. A.; Shakya, S. R. J. Org. Chem. 1994, 59, 3445.
24. 14 side chain: (a) Scott, J. W.; Bizzaro, F. T.; Parrish, D. R.; Saucy, G. Helv. Chim. Acta 1976, 59, 290. (b) Cohen, N.; Eichel, W. F.; Lopresh, R. J.; Neukom, C.; Saucy, G. J. Org. Chem. 1976, 41, 3505. (c) Fuganti, C.; Grasselli, P. J. Chem. Soc., Chem. Commun. 1979, 995. (d) Heathcock, C. H.; Jarvi, E. T. Tetrahedron Lett. 1982, 23, 2825. (e) Helmchen, G.; Schmierer, R. Tetrahedron Lett. 1983, 24, 1235. (f) Bérubé, G.; Deslongchamps P. Can. J. Chem. 1984, 62, 1558. (g) Bérubé, G.; Deslongchamps, P. Bull. Soc. Chim. Fr. 1987, 103. (h) Takano, S.; Shimazaki, Y.; Iwahushi, Y.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 3619. (i) Naoshima, Y.; Munakata, Y.; Yoshida, S.; Funai, A. J. Chem. Soc. Perkin Trans. 1 1991, 549. (j) Mori, K.; Harada, H.; Zagatti, P.; Cork, A.; Hall, D. R Liebigs Ann. Chem. 1991, 259. (k) Takabe, K; Sawada, H.; Satani, T.; Yamada, T.; Katagiri, T.; Yoda, H. Rioorg. Med. Chem. Lett. 1993, 3, 157. (l) Molander, G. A.; Shakya, S. R. J. Org. Chem. 1994, 59, 3445.
25. 14 side chain: (a) Scott, J. W.; Bizzaro, F. T.; Parrish, D. R.; Saucy, G. Helv. Chim. Acta 1976, 59, 290. (b) Cohen, N.; Eichel, W. F.; Lopresh, R. J.; Neukom, C.; Saucy, G. J. Org. Chem. 1976, 41, 3505. (c) Fuganti, C.; Grasselli, P. J. Chem. Soc., Chem. Commun. 1979, 995. (d) Heathcock, C. H.; Jarvi, E. T. Tetrahedron Lett. 1982, 23, 2825. (e) Helmchen, G.; Schmierer, R. Tetrahedron Lett. 1983, 24, 1235. (f) Bérubé, G.; Deslongchamps P. Can. J. Chem. 1984, 62, 1558. (g) Bérubé, G.; Deslongchamps, P. Bull. Soc. Chim. Fr. 1987, 103. (h) Takano, S.; Shimazaki, Y.; Iwahushi, Y.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 3619. (i) Naoshima, Y.; Munakata, Y.; Yoshida, S.; Funai, A. J. Chem. Soc. Perkin Trans. 1 1991, 549. (j) Mori, K.; Harada, H.; Zagatti, P.; Cork, A.; Hall, D. R Liebigs Ann. Chem. 1991, 259. (k) Takabe, K; Sawada, H.; Satani, T.; Yamada, T.; Katagiri, T.; Yoda, H. Rioorg. Med. Chem. Lett. 1993, 3, 157. (l) Molander, G. A.; Shakya, S. R. J. Org. Chem. 1994, 59, 3445.
26. 14 side chain: (a) Scott, J. W.; Bizzaro, F. T.; Parrish, D. R.; Saucy, G. Helv. Chim. Acta 1976, 59, 290. (b) Cohen, N.; Eichel, W. F.; Lopresh, R. J.; Neukom, C.; Saucy, G. J. Org. Chem. 1976, 41, 3505. (c) Fuganti, C.; Grasselli, P. J. Chem. Soc., Chem. Commun. 1979, 995. (d) Heathcock, C. H.; Jarvi, E. T. Tetrahedron Lett. 1982, 23, 2825. (e) Helmchen, G.; Schmierer, R. Tetrahedron Lett. 1983, 24, 1235. (f) Bérubé, G.; Deslongchamps P. Can. J. Chem. 1984, 62, 1558. (g) Bérubé, G.; Deslongchamps, P. Bull. Soc. Chim. Fr. 1987, 103. (h) Takano, S.; Shimazaki, Y.; Iwahushi, Y.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 3619. (i) Naoshima, Y.; Munakata, Y.; Yoshida, S.; Funai, A. J. Chem. Soc. Perkin Trans. 1 1991, 549. (j) Mori, K.; Harada, H.; Zagatti, P.; Cork, A.; Hall, D. R Liebigs Ann. Chem. 1991, 259. (k) Takabe, K; Sawada, H.; Satani, T.; Yamada, T.; Katagiri, T.; Yoda, H. Rioorg. Med. Chem. Lett. 1993, 3, 157. (l) Molander, G. A.; Shakya, S. R. J. Org. Chem. 1994, 59, 3445.
27. 15 side chain: (a) Schmid, M.; Barner, R. Helv. Chim. Acta 1979, 62, 464. (b) Zell, R. Helv. Chim. Acta 1979, 62, 474. (c) Cohen, N.; Lopresti, R. J.; Saucy, G. J. Am. Chem. Soc. 1979, 101, 6710. (d) Fujisawa, T.; Sato, T.; Kawara, T.; Ohashi, K Tetrahedron Lett. 1981, 22, 4823. (e) Trost, B. M.; Klum, T. P. J. Am. Chem. Soc. 1981, 103, 1864. (f) Koreeda, M.; Brown, L. J. Org. Chem. 1983, 48, 2122. (g) Fujiwara, J.; Fukutani, Y.; Hasegawa, M.; Muruoka. K.; Yamamoto, H. J. Am. Chem. Soc. 1984, 106, 5004. (h) Gramatica, P.; Manitto, P.; Monti, D.; Speranza, G. Tetrahedron 1986, 24, 6687. (i) Takaya, H.; Ohta, T.; Sayo, N.; Kumobayashi, A.; Akutagawa, S.; Inoue, S.; Kasahara, I.; Noyori. R. J. Am. Chem. Soc. 1987, 109, 1596. (j) Gould, T. J.; Balestra, M.; Wittman, M. D.; Gary, T. A.; Rossano, L. T.; Kallmerten, J. J. Org. Chem. 1987, 52, 3889. (k) Hübscher, J.; Barner, R. Helv. Chim. Acta 1990, 73, 1068. (l) Heiser, B.; Broger, E. A.; Crameri, Y. Tetrahedron Asymmetry 1991, 2, 51. (m) Takano, S.; Sugihara, T.; Ogasawara, K. Synlett. 1991, 279. (n) Cohen, N.; Schaer, G.; Scalone, M. J Org. Chem. 1992, 57, 5783.
28. 15 side chain: (a) Schmid, M.; Barner, R. Helv. Chim. Acta 1979, 62, 464. (b) Zell, R. Helv. Chim. Acta 1979, 62, 474. (c) Cohen, N.; Lopresti, R. J.; Saucy, G. J. Am. Chem. Soc. 1979, 101, 6710. (d) Fujisawa, T.; Sato, T.; Kawara, T.; Ohashi, K Tetrahedron Lett. 1981, 22, 4823. (e) Trost, B. M.; Klum, T. P. J. Am. Chem. Soc. 1981, 103, 1864. (f) Koreeda, M.; Brown, L. J. Org. Chem. 1983, 48, 2122. (g) Fujiwara, J.; Fukutani, Y.; Hasegawa, M.; Muruoka. K.; Yamamoto, H. J. Am. Chem. Soc. 1984, 106, 5004. (h) Gramatica, P.; Manitto, P.; Monti, D.; Speranza, G. Tetrahedron 1986, 24, 6687. (i) Takaya, H.; Ohta, T.; Sayo, N.; Kumobayashi, A.; Akutagawa, S.; Inoue, S.; Kasahara, I.; Noyori. R. J. Am. Chem. Soc. 1987, 109, 1596. (j) Gould, T. J.; Balestra, M.; Wittman, M. D.; Gary, T. A.; Rossano, L. T.; Kallmerten, J. J. Org. Chem. 1987, 52, 3889. (k) Hübscher, J.; Barner, R. Helv. Chim. Acta 1990, 73, 1068. (l) Heiser, B.; Broger, E. A.; Crameri, Y. Tetrahedron Asymmetry 1991, 2, 51. (m) Takano, S.; Sugihara, T.; Ogasawara, K. Synlett. 1991, 279. (n) Cohen, N.; Schaer, G.; Scalone, M. J Org. Chem. 1992, 57, 5783.
29. 15 side chain: (a) Schmid, M.; Barner, R. Helv. Chim. Acta 1979, 62, 464. (b) Zell, R. Helv. Chim. Acta 1979, 62, 474. (c) Cohen, N.; Lopresti, R. J.; Saucy, G. J. Am. Chem. Soc. 1979, 101, 6710. (d) Fujisawa, T.; Sato, T.; Kawara, T.; Ohashi, K Tetrahedron Lett. 1981, 22, 4823. (e) Trost, B. M.; Klum, T. P. J. Am. Chem. Soc. 1981, 103, 1864. (f) Koreeda, M.; Brown, L. J. Org. Chem. 1983, 48, 2122. (g) Fujiwara, J.; Fukutani, Y.; Hasegawa, M.; Muruoka. K.; Yamamoto, H. J. Am. Chem. Soc. 1984, 106, 5004. (h) Gramatica, P.; Manitto, P.; Monti, D.; Speranza, G. Tetrahedron 1986, 24, 6687. (i) Takaya, H.; Ohta, T.; Sayo, N.; Kumobayashi, A.; Akutagawa, S.; Inoue, S.; Kasahara, I.; Noyori. R. J. Am. Chem. Soc. 1987, 109, 1596. (j) Gould, T. J.; Balestra, M.; Wittman, M. D.; Gary, T. A.; Rossano, L. T.; Kallmerten, J. J. Org. Chem. 1987, 52, 3889. (k) Hübscher, J.; Barner, R. Helv. Chim. Acta 1990, 73, 1068. (l) Heiser, B.; Broger, E. A.; Crameri, Y. Tetrahedron Asymmetry 1991, 2, 51. (m) Takano, S.; Sugihara, T.; Ogasawara, K. Synlett. 1991, 279. (n) Cohen, N.; Schaer, G.; Scalone, M. J Org. Chem. 1992, 57, 5783.
30. 15 side chain: (a) Schmid, M.; Barner, R. Helv. Chim. Acta 1979, 62, 464. (b) Zell, R. Helv. Chim. Acta 1979, 62, 474. (c) Cohen, N.; Lopresti, R. J.; Saucy, G. J. Am. Chem. Soc. 1979, 101, 6710. (d) Fujisawa, T.; Sato, T.; Kawara, T.; Ohashi, K Tetrahedron Lett. 1981, 22, 4823. (e) Trost, B. M.; Klum, T. P. J. Am. Chem. Soc. 1981, 103, 1864. (f) Koreeda, M.; Brown, L. J. Org. Chem. 1983, 48, 2122. (g) Fujiwara, J.; Fukutani, Y.; Hasegawa, M.; Muruoka. K.; Yamamoto, H. J. Am. Chem. Soc. 1984, 106, 5004. (h) Gramatica, P.; Manitto, P.; Monti, D.; Speranza, G. Tetrahedron 1986, 24, 6687. (i) Takaya, H.; Ohta, T.; Sayo, N.; Kumobayashi, A.; Akutagawa, S.; Inoue, S.; Kasahara, I.; Noyori. R. J. Am. Chem. Soc. 1987, 109, 1596. (j) Gould, T. J.; Balestra, M.; Wittman, M. D.; Gary, T. A.; Rossano, L. T.; Kallmerten, J. J. Org. Chem. 1987, 52, 3889. (k) Hübscher, J.; Barner, R. Helv. Chim. Acta 1990, 73, 1068. (l) Heiser, B.; Broger, E. A.; Crameri, Y. Tetrahedron Asymmetry 1991, 2, 51. (m) Takano, S.; Sugihara, T.; Ogasawara, K. Synlett. 1991, 279. (n) Cohen, N.; Schaer, G.; Scalone, M. J Org. Chem. 1992, 57, 5783.
31. 15 side chain: (a) Schmid, M.; Barner, R. Helv. Chim. Acta 1979, 62, 464. (b) Zell, R. Helv. Chim. Acta 1979, 62, 474. (c) Cohen, N.; Lopresti, R. J.; Saucy, G. J. Am. Chem. Soc. 1979, 101, 6710. (d) Fujisawa, T.; Sato, T.; Kawara, T.; Ohashi, K Tetrahedron Lett. 1981, 22, 4823. (e) Trost, B. M.; Klum, T. P. J. Am. Chem. Soc. 1981, 103, 1864. (f) Koreeda, M.; Brown, L. J. Org. Chem. 1983, 48, 2122. (g) Fujiwara, J.; Fukutani, Y.; Hasegawa, M.; Muruoka. K.; Yamamoto, H. J. Am. Chem. Soc. 1984, 106, 5004. (h) Gramatica, P.; Manitto, P.; Monti, D.; Speranza, G. Tetrahedron 1986, 24, 6687. (i) Takaya, H.; Ohta, T.; Sayo, N.; Kumobayashi, A.; Akutagawa, S.; Inoue, S.; Kasahara, I.; Noyori. R. J. Am. Chem. Soc. 1987, 109, 1596. (j) Gould, T. J.; Balestra, M.; Wittman, M. D.; Gary, T. A.; Rossano, L. T.; Kallmerten, J. J. Org. Chem. 1987, 52, 3889. (k) Hübscher, J.; Barner, R. Helv. Chim. Acta 1990, 73, 1068. (l) Heiser, B.; Broger, E. A.; Crameri, Y. Tetrahedron Asymmetry 1991, 2, 51. (m) Takano, S.; Sugihara, T.; Ogasawara, K. Synlett. 1991, 279. (n) Cohen, N.; Schaer, G.; Scalone, M. J Org. Chem. 1992, 57, 5783.
32. 15 side chain: (a) Schmid, M.; Barner, R. Helv. Chim. Acta 1979, 62, 464. (b) Zell, R. Helv. Chim. Acta 1979, 62, 474. (c) Cohen, N.; Lopresti, R. J.; Saucy, G. J. Am. Chem. Soc. 1979, 101, 6710. (d) Fujisawa, T.; Sato, T.; Kawara, T.; Ohashi, K Tetrahedron Lett. 1981, 22, 4823. (e) Trost, B. M.; Klum, T. P. J. Am. Chem. Soc. 1981, 103, 1864. (f) Koreeda, M.; Brown, L. J. Org. Chem. 1983, 48, 2122. (g) Fujiwara, J.; Fukutani, Y.; Hasegawa, M.; Muruoka. K.; Yamamoto, H. J. Am. Chem. Soc. 1984, 106, 5004. (h) Gramatica, P.; Manitto, P.; Monti, D.; Speranza, G. Tetrahedron 1986, 24, 6687. (i) Takaya, H.; Ohta, T.; Sayo, N.; Kumobayashi, A.; Akutagawa, S.; Inoue, S.; Kasahara, I.; Noyori. R. J. Am. Chem. Soc. 1987, 109, 1596. (j) Gould, T. J.; Balestra, M.; Wittman, M. D.; Gary, T. A.; Rossano, L. T.; Kallmerten, J. J. Org. Chem. 1987, 52, 3889. (k) Hübscher, J.; Barner, R. Helv. Chim. Acta 1990, 73, 1068. (l) Heiser, B.; Broger, E. A.; Crameri, Y. Tetrahedron Asymmetry 1991, 2, 51. (m) Takano, S.; Sugihara, T.; Ogasawara, K. Synlett. 1991, 279. (n) Cohen, N.; Schaer, G.; Scalone, M. J Org. Chem. 1992, 57, 5783.
33. 15 side chain: (a) Schmid, M.; Barner, R. Helv. Chim. Acta 1979, 62, 464. (b) Zell, R. Helv. Chim. Acta 1979, 62, 474. (c) Cohen, N.; Lopresti, R. J.; Saucy, G. J. Am. Chem. Soc. 1979, 101, 6710. (d) Fujisawa, T.; Sato, T.; Kawara, T.; Ohashi, K Tetrahedron Lett. 1981, 22, 4823. (e) Trost, B. M.; Klum, T. P. J. Am. Chem. Soc. 1981, 103, 1864. (f) Koreeda, M.; Brown, L. J. Org. Chem. 1983, 48, 2122. (g) Fujiwara, J.; Fukutani, Y.; Hasegawa, M.; Muruoka. K.; Yamamoto, H. J. Am. Chem. Soc. 1984, 106, 5004. (h) Gramatica, P.; Manitto, P.; Monti, D.; Speranza, G. Tetrahedron 1986, 24, 6687. (i) Takaya, H.; Ohta, T.; Sayo, N.; Kumobayashi, A.; Akutagawa, S.; Inoue, S.; Kasahara, I.; Noyori. R. J. Am. Chem. Soc. 1987, 109, 1596. (j) Gould, T. J.; Balestra, M.; Wittman, M. D.; Gary, T. A.; Rossano, L. T.; Kallmerten, J. J. Org. Chem. 1987, 52, 3889. (k) Hübscher, J.; Barner, R. Helv. Chim. Acta 1990, 73, 1068. (l) Heiser, B.; Broger, E. A.; Crameri, Y. Tetrahedron Asymmetry 1991, 2, 51. (m) Takano, S.; Sugihara, T.; Ogasawara, K. Synlett. 1991, 279. (n) Cohen, N.; Schaer, G.; Scalone, M. J Org. Chem. 1992, 57, 5783.
34. 15 side chain: (a) Schmid, M.; Barner, R. Helv. Chim. Acta 1979, 62, 464. (b) Zell, R. Helv. Chim. Acta 1979, 62, 474. (c) Cohen, N.; Lopresti, R. J.; Saucy, G. J. Am. Chem. Soc. 1979, 101, 6710. (d) Fujisawa, T.; Sato, T.; Kawara, T.; Ohashi, K Tetrahedron Lett. 1981, 22, 4823. (e) Trost, B. M.; Klum, T. P. J. Am. Chem. Soc. 1981, 103, 1864. (f) Koreeda, M.; Brown, L. J. Org. Chem. 1983, 48, 2122. (g) Fujiwara, J.; Fukutani, Y.; Hasegawa, M.; Muruoka. K.; Yamamoto, H. J. Am. Chem. Soc. 1984, 106, 5004. (h) Gramatica, P.; Manitto, P.; Monti, D.; Speranza, G. Tetrahedron 1986, 24, 6687. (i) Takaya, H.; Ohta, T.; Sayo, N.; Kumobayashi, A.; Akutagawa, S.; Inoue, S.; Kasahara, I.; Noyori. R. J. Am. Chem. Soc. 1987, 109, 1596. (j) Gould, T. J.; Balestra, M.; Wittman, M. D.; Gary, T. A.; Rossano, L. T.; Kallmerten, J. J. Org. Chem. 1987, 52, 3889. (k) Hübscher, J.; Barner, R. Helv. Chim. Acta 1990, 73, 1068. (l) Heiser, B.; Broger, E. A.; Crameri, Y. Tetrahedron Asymmetry 1991, 2, 51. (m) Takano, S.; Sugihara, T.; Ogasawara, K. Synlett. 1991, 279. (n) Cohen, N.; Schaer, G.; Scalone, M. J Org. Chem. 1992, 57, 5783.
35. 15 side chain: (a) Schmid, M.; Barner, R. Helv. Chim. Acta 1979, 62, 464. (b) Zell, R. Helv. Chim. Acta 1979, 62, 474. (c) Cohen, N.; Lopresti, R. J.; Saucy, G. J. Am. Chem. Soc. 1979, 101, 6710. (d) Fujisawa, T.; Sato, T.; Kawara, T.; Ohashi, K Tetrahedron Lett. 1981, 22, 4823. (e) Trost, B. M.; Klum, T. P. J. Am. Chem. Soc. 1981, 103, 1864. (f) Koreeda, M.; Brown, L. J. Org. Chem. 1983, 48, 2122. (g) Fujiwara, J.; Fukutani, Y.; Hasegawa, M.; Muruoka. K.; Yamamoto, H. J. Am. Chem. Soc. 1984, 106, 5004. (h) Gramatica, P.; Manitto, P.; Monti, D.; Speranza, G. Tetrahedron 1986, 24, 6687. (i) Takaya, H.; Ohta, T.; Sayo, N.; Kumobayashi, A.; Akutagawa, S.; Inoue, S.; Kasahara, I.; Noyori. R. J. Am. Chem. Soc. 1987, 109, 1596. (j) Gould, T. J.; Balestra, M.; Wittman, M. D.; Gary, T. A.; Rossano, L. T.; Kallmerten, J. J. Org. Chem. 1987, 52, 3889. (k) Hübscher, J.; Barner, R. Helv. Chim. Acta 1990, 73, 1068. (l) Heiser, B.; Broger, E. A.; Crameri, Y. Tetrahedron Asymmetry 1991, 2, 51. (m) Takano, S.; Sugihara, T.; Ogasawara, K. Synlett. 1991, 279. (n) Cohen, N.; Schaer, G.; Scalone, M. J Org. Chem. 1992, 57, 5783.
36. 15 side chain: (a) Schmid, M.; Barner, R. Helv. Chim. Acta 1979, 62, 464. (b) Zell, R. Helv. Chim. Acta 1979, 62, 474. (c) Cohen, N.; Lopresti, R. J.; Saucy, G. J. Am. Chem. Soc. 1979, 101, 6710. (d) Fujisawa, T.; Sato, T.; Kawara, T.; Ohashi, K Tetrahedron Lett. 1981, 22, 4823. (e) Trost, B. M.; Klum, T. P. J. Am. Chem. Soc. 1981, 103, 1864. (f) Koreeda, M.; Brown, L. J. Org. Chem. 1983, 48, 2122. (g) Fujiwara, J.; Fukutani, Y.; Hasegawa, M.; Muruoka. K.; Yamamoto, H. J. Am. Chem. Soc. 1984, 106, 5004. (h) Gramatica, P.; Manitto, P.; Monti, D.; Speranza, G. Tetrahedron 1986, 24, 6687. (i) Takaya, H.; Ohta, T.; Sayo, N.; Kumobayashi, A.; Akutagawa, S.; Inoue, S.; Kasahara, I.; Noyori. R. J. Am. Chem. Soc. 1987, 109, 1596. (j) Gould, T. J.; Balestra, M.; Wittman, M. D.; Gary, T. A.; Rossano, L. T.; Kallmerten, J. J. Org. Chem. 1987, 52, 3889. (k) Hübscher, J.; Barner, R. Helv. Chim. Acta 1990, 73, 1068. (l) Heiser, B.; Broger, E. A.; Crameri, Y. Tetrahedron Asymmetry 1991, 2, 51. (m) Takano, S.; Sugihara, T.; Ogasawara, K. Synlett. 1991, 279. (n) Cohen, N.; Schaer, G.; Scalone, M. J Org. Chem. 1992, 57, 5783.
37. 15 side chain: (a) Schmid, M.; Barner, R. Helv. Chim. Acta 1979, 62, 464. (b) Zell, R. Helv. Chim. Acta 1979, 62, 474. (c) Cohen, N.; Lopresti, R. J.; Saucy, G. J. Am. Chem. Soc. 1979, 101, 6710. (d) Fujisawa, T.; Sato, T.; Kawara, T.; Ohashi, K Tetrahedron Lett. 1981, 22, 4823. (e) Trost, B. M.; Klum, T. P. J. Am. Chem. Soc. 1981, 103, 1864. (f) Koreeda, M.; Brown, L. J. Org. Chem. 1983, 48, 2122. (g) Fujiwara, J.; Fukutani, Y.; Hasegawa, M.; Muruoka. K.; Yamamoto, H. J. Am. Chem. Soc. 1984, 106, 5004. (h) Gramatica, P.; Manitto, P.; Monti, D.; Speranza, G. Tetrahedron 1986, 24, 6687. (i) Takaya, H.; Ohta, T.; Sayo, N.; Kumobayashi, A.; Akutagawa, S.; Inoue, S.; Kasahara, I.; Noyori. R. J. Am. Chem. Soc. 1987, 109, 1596. (j) Gould, T. J.; Balestra, M.; Wittman, M. D.; Gary, T. A.; Rossano, L. T.; Kallmerten, J. J. Org. Chem. 1987, 52, 3889. (k) Hübscher, J.; Barner, R. Helv. Chim. Acta 1990, 73, 1068. (l) Heiser, B.; Broger, E. A.; Crameri, Y. Tetrahedron Asymmetry 1991, 2, 51. (m) Takano, S.; Sugihara, T.; Ogasawara, K. Synlett. 1991, 279. (n) Cohen, N.; Schaer, G.; Scalone, M. J Org. Chem. 1992, 57, 5783.
38. 15 side chain: (a) Schmid, M.; Barner, R. Helv. Chim. Acta 1979, 62, 464. (b) Zell, R. Helv. Chim. Acta 1979, 62, 474. (c) Cohen, N.; Lopresti, R. J.; Saucy, G. J. Am. Chem. Soc. 1979, 101, 6710. (d) Fujisawa, T.; Sato, T.; Kawara, T.; Ohashi, K Tetrahedron Lett. 1981, 22, 4823. (e) Trost, B. M.; Klum, T. P. J. Am. Chem. Soc. 1981, 103, 1864. (f) Koreeda, M.; Brown, L. J. Org. Chem. 1983, 48, 2122. (g) Fujiwara, J.; Fukutani, Y.; Hasegawa, M.; Muruoka. K.; Yamamoto, H. J. Am. Chem. Soc. 1984, 106, 5004. (h) Gramatica, P.; Manitto, P.; Monti, D.; Speranza, G. Tetrahedron 1986, 24, 6687. (i) Takaya, H.; Ohta, T.; Sayo, N.; Kumobayashi, A.; Akutagawa, S.; Inoue, S.; Kasahara, I.; Noyori. R. J. Am. Chem. Soc. 1987, 109, 1596. (j) Gould, T. J.; Balestra, M.; Wittman, M. D.; Gary, T. A.; Rossano, L. T.; Kallmerten, J. J. Org. Chem. 1987, 52, 3889. (k) Hübscher, J.; Barner, R. Helv. Chim. Acta 1990, 73, 1068. (l) Heiser, B.; Broger, E. A.; Crameri, Y. Tetrahedron Asymmetry 1991, 2, 51. (m) Takano, S.; Sugihara, T.; Ogasawara, K. Synlett. 1991, 279. (n) Cohen, N.; Schaer, G.; Scalone, M. J Org. Chem. 1992, 57, 5783.
39. 15 side chain: (a) Schmid, M.; Barner, R. Helv. Chim. Acta 1979, 62, 464. (b) Zell, R. Helv. Chim. Acta 1979, 62, 474. (c) Cohen, N.; Lopresti, R. J.; Saucy, G. J. Am. Chem. Soc. 1979, 101, 6710. (d) Fujisawa, T.; Sato, T.; Kawara, T.; Ohashi, K Tetrahedron Lett. 1981, 22, 4823. (e) Trost, B. M.; Klum, T. P. J. Am. Chem. Soc. 1981, 103, 1864. (f) Koreeda, M.; Brown, L. J. Org. Chem. 1983, 48, 2122. (g) Fujiwara, J.; Fukutani, Y.; Hasegawa, M.; Muruoka. K.; Yamamoto, H. J. Am. Chem. Soc. 1984, 106, 5004. (h) Gramatica, P.; Manitto, P.; Monti, D.; Speranza, G. Tetrahedron 1986, 24, 6687. (i) Takaya, H.; Ohta, T.; Sayo, N.; Kumobayashi, A.; Akutagawa, S.; Inoue, S.; Kasahara, I.; Noyori. R. J. Am. Chem. Soc. 1987, 109, 1596. (j) Gould, T. J.; Balestra, M.; Wittman, M. D.; Gary, T. A.; Rossano, L. T.; Kallmerten, J. J. Org. Chem. 1987, 52, 3889. (k) Hübscher, J.; Barner, R. Helv. Chim. Acta 1990, 73, 1068. (l) Heiser, B.; Broger, E. A.; Crameri, Y. Tetrahedron Asymmetry 1991, 2, 51. (m) Takano, S.; Sugihara, T.; Ogasawara, K. Synlett. 1991, 279. (n) Cohen, N.; Schaer, G.; Scalone, M. J Org. Chem. 1992, 57, 5783.
40. 15 side chain: (a) Schmid, M.; Barner, R. Helv. Chim. Acta 1979, 62, 464. (b) Zell, R. Helv. Chim. Acta 1979, 62, 474. (c) Cohen, N.; Lopresti, R. J.; Saucy, G. J. Am. Chem. Soc. 1979, 101, 6710. (d) Fujisawa, T.; Sato, T.; Kawara, T.; Ohashi, K Tetrahedron Lett. 1981, 22, 4823. (e) Trost, B. M.; Klum, T. P. J. Am. Chem. Soc. 1981, 103, 1864. (f) Koreeda, M.; Brown, L. J. Org. Chem. 1983, 48, 2122. (g) Fujiwara, J.; Fukutani, Y.; Hasegawa, M.; Muruoka. K.; Yamamoto, H. J. Am. Chem. Soc. 1984, 106, 5004. (h) Gramatica, P.; Manitto, P.; Monti, D.; Speranza, G. Tetrahedron 1986, 24, 6687. (i) Takaya, H.; Ohta, T.; Sayo, N.; Kumobayashi, A.; Akutagawa, S.; Inoue, S.; Kasahara, I.; Noyori. R. J. Am. Chem. Soc. 1987, 109, 1596. (j) Gould, T. J.; Balestra, M.; Wittman, M. D.; Gary, T. A.; Rossano, L. T.; Kallmerten, J. J. Org. Chem. 1987, 52, 3889. (k) Hübscher, J.; Barner, R. Helv. Chim. Acta 1990, 73, 1068. (l) Heiser, B.; Broger, E. A.; Crameri, Y. Tetrahedron Asymmetry 1991, 2, 51. (m) Takano, S.; Sugihara, T.; Ogasawara, K. Synlett. 1991, 279. (n) Cohen, N.; Schaer, G.; Scalone, M. J Org. Chem. 1992, 57, 5783.
41. (a) CReskis, B. A.; Lebedeva, K. V.; Moiseenkov, A. M. Izv. Akad Nauk. SSSH, Ser. Khim. 1988, 4, 865.
42. (b) Moiseenkov, A. M.; Cheskis, B. A. Dokl. Akad. Nauk. SSSR 1986, 230, 1379.
43. For other synthesis of tribolure, see: (a) Mori, K.; Kuwahara, S.; Ueda, H. Tetrahedron 1983, 39, 2439. (b) Fuganti, C.; Grasselli, P.; Servi, S.; Högberg, H. E. J. Chem. Soc., Perkin Trans. 1 1988, 3061. (c) Mori, K.; Takikawa, H. Liebigs Ann. Chem. 1991, 497.
44. For other synthesis of tribolure, see: (a) Mori, K.; Kuwahara, S.; Ueda, H. Tetrahedron 1983, 39, 2439. (b) Fuganti, C.; Grasselli, P.; Servi, S.; Högberg, H. E. J. Chem. Soc., Perkin Trans. 1 1988, 3061. (c) Mori, K.; Takikawa, H. Liebigs Ann. Chem. 1991, 497.
45. For other synthesis of tribolure, see: (a) Mori, K.; Kuwahara, S.; Ueda, H. Tetrahedron 1983, 39, 2439. (b) Fuganti, C.; Grasselli, P.; Servi, S.; Högberg, H. E. J. Chem. Soc., Perkin Trans. 1 1988, 3061. (c) Mori, K.; Takikawa, H. Liebigs Ann. Chem. 1991, 497.