Total synthesis of (-)-reserpine using the chiron approach

Journal of Organic Chemistry

Volumn 62, Issue 3, 1997, Pages 465-473

  Hanessian, Stephen ^a   Pan, Jingwen ^a   Carnell, Andrew ^a   Bouchard, Hervé ^a   Lesage, Luc ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

RESERPINE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031029295     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961713w     Document Type: Article

References (84)

1. For some authoritative monographs, see Nicolaou, K. C.; Sorensen, L. E. in Classics in Organic Synthesis; VCH: New York, 1996. Corey, E. J.; Cheng, X.-M. The Logic of Chemical Synthesis; Wiley: New York, 1989. Strategies and Tactics in Organic Synthesis; Lindberg, T., Ed.; Academic: San Diego, CA 1991, Vols 1-3. Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, The Netherlands, 1994; Vols. 1-14.
2. For some authoritative monographs, see Nicolaou, K. C.; Sorensen, L. E. in Classics in Organic Synthesis; VCH: New York, 1996. Corey, E. J.; Cheng, X.-M. The Logic of Chemical Synthesis; Wiley: New York, 1989. Strategies and Tactics in Organic Synthesis; Lindberg, T., Ed.; Academic: San Diego, CA 1991, Vols 1-3. Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, The Netherlands, 1994; Vols. 1-14.
3. For some authoritative monographs, see Nicolaou, K. C.; Sorensen, L. E. in Classics in Organic Synthesis; VCH: New York, 1996. Corey, E. J.; Cheng, X.-M. The Logic of Chemical Synthesis; Wiley: New York, 1989. Strategies and Tactics in Organic Synthesis; Lindberg, T., Ed.; Academic: San Diego, CA 1991, Vols 1-3. Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, The Netherlands, 1994; Vols. 1-14.
4. For some authoritative monographs, see Nicolaou, K. C.; Sorensen, L. E. in Classics in Organic Synthesis; VCH: New York, 1996. Corey, E. J.; Cheng, X.-M. The Logic of Chemical Synthesis; Wiley: New York, 1989. Strategies and Tactics in Organic Synthesis; Lindberg, T., Ed.; Academic: San Diego, CA 1991, Vols 1-3. Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, The Netherlands, 1994; Vols. 1-14.
5. Woodward, R. B.; Bader, F. E.; Bickel, H.; Frey, A. J.; Kierstead, R. W. J. Am. Chem. Soc. 1956, 78, 2023, 2657. Tetrahedron 1958, 2, 1. Woodward, R. B. In Perspectives in Organic Syntheses; Todd, A. R., Ed., Interscience: New York, 1956.
6. Woodward, R. B.; Bader, F. E.; Bickel, H.; Frey, A. J.; Kierstead, R. W. J. Am. Chem. Soc. 1956, 78, 2023, 2657. Tetrahedron 1958, 2, 1. Woodward, R. B. In Perspectives in Organic Syntheses; Todd, A. R., Ed., Interscience: New York, 1956.
7. Woodward, R. B.; Bader, F. E.; Bickel, H.; Frey, A. J.; Kierstead, R. W. J. Am. Chem. Soc. 1956, 78, 2023, 2657. Tetrahedron 1958, 2, 1. Woodward, R. B. In Perspectives in Organic Syntheses; Todd, A. R., Ed., Interscience: New York, 1956.
8. For representative examples, see (a) Wenkert, E.; Liu, L. H.; Johnston, D. B. R. J. Org. Chem. 1965, 30, 722. Heterocycles 1984, 21, 325. (b) Takano, S.; Ito, F.; Ogasawara, K. Heterocycles 1980, 14, 453. (c) Suzuki, T.; Tomino, A.; Unno, K.; Kametani, T. Chem. Pharm. Bull. Jpn. 1981, 29, 76. Suzuki, T.; Tomino, A.; Unno, K.; Kametani, T. Heterocycles 1980, 14, 439. (d) Chao, S.; Kunng, F.-A.; Gu, J.-M.; Ammon, H. L.; Mariano, P. S. J. Org. Chem. 1984, 49, 2708. (e) Wenkert, E. Heterocycles 1984, 21, 325. (f) Jung, M. E.; Light, L. A. J. Am. Chem. Soc. 1984, 106, 7614. (g) Isobe, M.; Fukami, N.; Nishikawa, T.; Goto, T. Heterocycles 1987, 25, 521. (h) Polniaszek, R. P.; Stevens, R. V. J. Org. Chem. 1986, 51, 3023. Szantay, C.; Blasko, G.; Honty, K.; Baitz-Gacs, E.; Toke, L. Liebigs Ann. Chem. 1983, 1269.
9. For representative examples, see (a) Wenkert, E.; Liu, L. H.; Johnston, D. B. R. J. Org. Chem. 1965, 30, 722. Heterocycles 1984, 21, 325. (b) Takano, S.; Ito, F.; Ogasawara, K. Heterocycles 1980, 14, 453. (c) Suzuki, T.; Tomino, A.; Unno, K.; Kametani, T. Chem. Pharm. Bull. Jpn. 1981, 29, 76. Suzuki, T.; Tomino, A.; Unno, K.; Kametani, T. Heterocycles 1980, 14, 439. (d) Chao, S.; Kunng, F.-A.; Gu, J.-M.; Ammon, H. L.; Mariano, P. S. J. Org. Chem. 1984, 49, 2708. (e) Wenkert, E. Heterocycles 1984, 21, 325. (f) Jung, M. E.; Light, L. A. J. Am. Chem. Soc. 1984, 106, 7614. (g) Isobe, M.; Fukami, N.; Nishikawa, T.; Goto, T. Heterocycles 1987, 25, 521. (h) Polniaszek, R. P.; Stevens, R. V. J. Org. Chem. 1986, 51, 3023. Szantay, C.; Blasko, G.; Honty, K.; Baitz-Gacs, E.; Toke, L. Liebigs Ann. Chem. 1983, 1269.
10. For representative examples, see (a) Wenkert, E.; Liu, L. H.; Johnston, D. B. R. J. Org. Chem. 1965, 30, 722. Heterocycles 1984, 21, 325. (b) Takano, S.; Ito, F.; Ogasawara, K. Heterocycles 1980, 14, 453. (c) Suzuki, T.; Tomino, A.; Unno, K.; Kametani, T. Chem. Pharm. Bull. Jpn. 1981, 29, 76. Suzuki, T.; Tomino, A.; Unno, K.; Kametani, T. Heterocycles 1980, 14, 439. (d) Chao, S.; Kunng, F.-A.; Gu, J.-M.; Ammon, H. L.; Mariano, P. S. J. Org. Chem. 1984, 49, 2708. (e) Wenkert, E. Heterocycles 1984, 21, 325. (f) Jung, M. E.; Light, L. A. J. Am. Chem. Soc. 1984, 106, 7614. (g) Isobe, M.; Fukami, N.; Nishikawa, T.; Goto, T. Heterocycles 1987, 25, 521. (h) Polniaszek, R. P.; Stevens, R. V. J. Org. Chem. 1986, 51, 3023. Szantay, C.; Blasko, G.; Honty, K.; Baitz-Gacs, E.; Toke, L. Liebigs Ann. Chem. 1983, 1269.
11. For representative examples, see (a) Wenkert, E.; Liu, L. H.; Johnston, D. B. R. J. Org. Chem. 1965, 30, 722. Heterocycles 1984, 21, 325. (b) Takano, S.; Ito, F.; Ogasawara, K. Heterocycles 1980, 14, 453. (c) Suzuki, T.; Tomino, A.; Unno, K.; Kametani, T. Chem. Pharm. Bull. Jpn. 1981, 29, 76. Suzuki, T.; Tomino, A.; Unno, K.; Kametani, T. Heterocycles 1980, 14, 439. (d) Chao, S.; Kunng, F.-A.; Gu, J.-M.; Ammon, H. L.; Mariano, P. S. J. Org. Chem. 1984, 49, 2708. (e) Wenkert, E. Heterocycles 1984, 21, 325. (f) Jung, M. E.; Light, L. A. J. Am. Chem. Soc. 1984, 106, 7614. (g) Isobe, M.; Fukami, N.; Nishikawa, T.; Goto, T. Heterocycles 1987, 25, 521. (h) Polniaszek, R. P.; Stevens, R. V. J. Org. Chem. 1986, 51, 3023. Szantay, C.; Blasko, G.; Honty, K.; Baitz-Gacs, E.; Toke, L. Liebigs Ann. Chem. 1983, 1269.
12. For representative examples, see (a) Wenkert, E.; Liu, L. H.; Johnston, D. B. R. J. Org. Chem. 1965, 30, 722. Heterocycles 1984, 21, 325. (b) Takano, S.; Ito, F.; Ogasawara, K. Heterocycles 1980, 14, 453. (c) Suzuki, T.; Tomino, A.; Unno, K.; Kametani, T. Chem. Pharm. Bull. Jpn. 1981, 29, 76. Suzuki, T.; Tomino, A.; Unno, K.; Kametani, T. Heterocycles 1980, 14, 439. (d) Chao, S.; Kunng, F.-A.; Gu, J.-M.; Ammon, H. L.; Mariano, P. S. J. Org. Chem. 1984, 49, 2708. (e) Wenkert, E. Heterocycles 1984, 21, 325. (f) Jung, M. E.; Light, L. A. J. Am. Chem. Soc. 1984, 106, 7614. (g) Isobe, M.; Fukami, N.; Nishikawa, T.; Goto, T. Heterocycles 1987, 25, 521. (h) Polniaszek, R. P.; Stevens, R. V. J. Org. Chem. 1986, 51, 3023. Szantay, C.; Blasko, G.; Honty, K.; Baitz-Gacs, E.; Toke, L. Liebigs Ann. Chem. 1983, 1269.
13. For representative examples, see (a) Wenkert, E.; Liu, L. H.; Johnston, D. B. R. J. Org. Chem. 1965, 30, 722. Heterocycles 1984, 21, 325. (b) Takano, S.; Ito, F.; Ogasawara, K. Heterocycles 1980, 14, 453. (c) Suzuki, T.; Tomino, A.; Unno, K.; Kametani, T. Chem. Pharm. Bull. Jpn. 1981, 29, 76. Suzuki, T.; Tomino, A.; Unno, K.; Kametani, T. Heterocycles 1980, 14, 439. (d) Chao, S.; Kunng, F.-A.; Gu, J.-M.; Ammon, H. L.; Mariano, P. S. J. Org. Chem. 1984, 49, 2708. (e) Wenkert, E. Heterocycles 1984, 21, 325. (f) Jung, M. E.; Light, L. A. J. Am. Chem. Soc. 1984, 106, 7614. (g) Isobe, M.; Fukami, N.; Nishikawa, T.; Goto, T. Heterocycles 1987, 25, 521. (h) Polniaszek, R. P.; Stevens, R. V. J. Org. Chem. 1986, 51, 3023. Szantay, C.; Blasko, G.; Honty, K.; Baitz-Gacs, E.; Toke, L. Liebigs Ann. Chem. 1983, 1269.
14. For representative examples, see (a) Wenkert, E.; Liu, L. H.; Johnston, D. B. R. J. Org. Chem. 1965, 30, 722. Heterocycles 1984, 21, 325. (b) Takano, S.; Ito, F.; Ogasawara, K. Heterocycles 1980, 14, 453. (c) Suzuki, T.; Tomino, A.; Unno, K.; Kametani, T. Chem. Pharm. Bull. Jpn. 1981, 29, 76. Suzuki, T.; Tomino, A.; Unno, K.; Kametani, T. Heterocycles 1980, 14, 439. (d) Chao, S.; Kunng, F.-A.; Gu, J.-M.; Ammon, H. L.; Mariano, P. S. J. Org. Chem. 1984, 49, 2708. (e) Wenkert, E. Heterocycles 1984, 21, 325. (f) Jung, M. E.; Light, L. A. J. Am. Chem. Soc. 1984, 106, 7614. (g) Isobe, M.; Fukami, N.; Nishikawa, T.; Goto, T. Heterocycles 1987, 25, 521. (h) Polniaszek, R. P.; Stevens, R. V. J. Org. Chem. 1986, 51, 3023. Szantay, C.; Blasko, G.; Honty, K.; Baitz-Gacs, E.; Toke, L. Liebigs Ann. Chem. 1983, 1269.
15. For representative examples, see (a) Wenkert, E.; Liu, L. H.; Johnston, D. B. R. J. Org. Chem. 1965, 30, 722. Heterocycles 1984, 21, 325. (b) Takano, S.; Ito, F.; Ogasawara, K. Heterocycles 1980, 14, 453. (c) Suzuki, T.; Tomino, A.; Unno, K.; Kametani, T. Chem. Pharm. Bull. Jpn. 1981, 29, 76. Suzuki, T.; Tomino, A.; Unno, K.; Kametani, T. Heterocycles 1980, 14, 439. (d) Chao, S.; Kunng, F.-A.; Gu, J.-M.; Ammon, H. L.; Mariano, P. S. J. Org. Chem. 1984, 49, 2708. (e) Wenkert, E. Heterocycles 1984, 21, 325. (f) Jung, M. E.; Light, L. A. J. Am. Chem. Soc. 1984, 106, 7614. (g) Isobe, M.; Fukami, N.; Nishikawa, T.; Goto, T. Heterocycles 1987, 25, 521. (h) Polniaszek, R. P.; Stevens, R. V. J. Org. Chem. 1986, 51, 3023. Szantay, C.; Blasko, G.; Honty, K.; Baitz-Gacs, E.; Toke, L. Liebigs Ann. Chem. 1983, 1269.
16. For representative examples, see (a) Wenkert, E.; Liu, L. H.; Johnston, D. B. R. J. Org. Chem. 1965, 30, 722. Heterocycles 1984, 21, 325. (b) Takano, S.; Ito, F.; Ogasawara, K. Heterocycles 1980, 14, 453. (c) Suzuki, T.; Tomino, A.; Unno, K.; Kametani, T. Chem. Pharm. Bull. Jpn. 1981, 29, 76. Suzuki, T.; Tomino, A.; Unno, K.; Kametani, T. Heterocycles 1980, 14, 439. (d) Chao, S.; Kunng, F.-A.; Gu, J.-M.; Ammon, H. L.; Mariano, P. S. J. Org. Chem. 1984, 49, 2708. (e) Wenkert, E. Heterocycles 1984, 21, 325. (f) Jung, M. E.; Light, L. A. J. Am. Chem. Soc. 1984, 106, 7614. (g) Isobe, M.; Fukami, N.; Nishikawa, T.; Goto, T. Heterocycles 1987, 25, 521. (h) Polniaszek, R. P.; Stevens, R. V. J. Org. Chem. 1986, 51, 3023. Szantay, C.; Blasko, G.; Honty, K.; Baitz-Gacs, E.; Toke, L. Liebigs Ann. Chem. 1983, 1269.
17. For representative examples, see (a) Wenkert, E.; Liu, L. H.; Johnston, D. B. R. J. Org. Chem. 1965, 30, 722. Heterocycles 1984, 21, 325. (b) Takano, S.; Ito, F.; Ogasawara, K. Heterocycles 1980, 14, 453. (c) Suzuki, T.; Tomino, A.; Unno, K.; Kametani, T. Chem. Pharm. Bull. Jpn. 1981, 29, 76. Suzuki, T.; Tomino, A.; Unno, K.; Kametani, T. Heterocycles 1980, 14, 439. (d) Chao, S.; Kunng, F.-A.; Gu, J.-M.; Ammon, H. L.; Mariano, P. S. J. Org. Chem. 1984, 49, 2708. (e) Wenkert, E. Heterocycles 1984, 21, 325. (f) Jung, M. E.; Light, L. A. J. Am. Chem. Soc. 1984, 106, 7614. (g) Isobe, M.; Fukami, N.; Nishikawa, T.; Goto, T. Heterocycles 1987, 25, 521. (h) Polniaszek, R. P.; Stevens, R. V. J. Org. Chem. 1986, 51, 3023. Szantay, C.; Blasko, G.; Honty, K.; Baitz-Gacs, E.; Toke, L. Liebigs Ann. Chem. 1983, 1269.
18. For representative examples, see (a) Wenkert, E.; Liu, L. H.; Johnston, D. B. R. J. Org. Chem. 1965, 30, 722. Heterocycles 1984, 21, 325. (b) Takano, S.; Ito, F.; Ogasawara, K. Heterocycles 1980, 14, 453. (c) Suzuki, T.; Tomino, A.; Unno, K.; Kametani, T. Chem. Pharm. Bull. Jpn. 1981, 29, 76. Suzuki, T.; Tomino, A.; Unno, K.; Kametani, T. Heterocycles 1980, 14, 439. (d) Chao, S.; Kunng, F.-A.; Gu, J.-M.; Ammon, H. L.; Mariano, P. S. J. Org. Chem. 1984, 49, 2708. (e) Wenkert, E. Heterocycles 1984, 21, 325. (f) Jung, M. E.; Light, L. A. J. Am. Chem. Soc. 1984, 106, 7614. (g) Isobe, M.; Fukami, N.; Nishikawa, T.; Goto, T. Heterocycles 1987, 25, 521. (h) Polniaszek, R. P.; Stevens, R. V. J. Org. Chem. 1986, 51, 3023. Szantay, C.; Blasko, G.; Honty, K.; Baitz-Gacs, E.; Toke, L. Liebigs Ann. Chem. 1983, 1269.
19. Stork, G. Pure Appl. Chem. 1989, 61, 439.
20. Gomez, A. M.; Lopez, J. C.; Fraser Reid, B. J. Org. Chem. 1994, 59, 4048.
21. Pearlman, B. A. J. Am. Chem. Soc. 1979, 101, 6398, 6404.
22. Wender, P. A.; Schaus, J. M.; White, A. W. J. Am. Chem. Soc. 1980, 102, 6157. Heterocycles 1987, 25, 263. Wender, P. A.; Schaus, J. M.; Torney, D. C. Tetrahedron Lett. 1979, 2485.
23. Wender, P. A.; Schaus, J. M.; White, A. W. J. Am. Chem. Soc. 1980, 102, 6157. Heterocycles 1987, 25, 263. Wender, P. A.; Schaus, J. M.; Torney, D. C. Tetrahedron Lett. 1979, 2485.
24. Wender, P. A.; Schaus, J. M.; White, A. W. J. Am. Chem. Soc. 1980, 102, 6157. Heterocycles 1987, 25, 263. Wender, P. A.; Schaus, J. M.; Torney, D. C. Tetrahedron Lett. 1979, 2485.
25. Martin, S. F.; Rueger, H.; Williamson, S. A.; Grzejszczak, S. J. Am. Chem. Soc. 1987, 109, 6124. Martin, S. F.; Grzejszczak, S.; Rueger, H.; Williamson, S. A. J. Am. Chem. Soc. 1985, 107, 4072.
26. Martin, S. F.; Rueger, H.; Williamson, S. A.; Grzejszczak, S. J. Am. Chem. Soc. 1987, 109, 6124. Martin, S. F.; Grzejszczak, S.; Rueger, H.; Williamson, S. A. J. Am. Chem. Soc. 1985, 107, 4072.
27. Zhang, L. H.; Gupta, A. K. and Cook, J. M. J. Org. Chem. 1989, 54, 4708. Gaskell, A. J.; Joule, J. A. Tetrahedron 1967, 23, 4053.
28. Zhang, L. H.; Gupta, A. K. and Cook, J. M. J. Org. Chem. 1989, 54, 4708. Gaskell, A. J.; Joule, J. A. Tetrahedron 1967, 23, 4053.
29. For the total synthesis of deserpidine see (a) Szantay, C.; Blaskó, G.; Honty, K.; Baitz-Gacs, E.; Toke, L. Liebigs Ann. Chem. 1983, 1292. (b) Miyata, O.; Hirata, Y.; Naito, T.; Ninomiya, I. Heterocycles 1984, 22, 1041; see also Gaskell, A. J.; Joule, J. A. Tetrahedron 1967, 23, 4053. Sakai, S.; Ogawa, M. Heterocycles 1978, 10, 67.
30. For the total synthesis of deserpidine see (a) Szantay, C.; Blaskó, G.; Honty, K.; Baitz-Gacs, E.; Toke, L. Liebigs Ann. Chem. 1983, 1292. (b) Miyata, O.; Hirata, Y.; Naito, T.; Ninomiya, I. Heterocycles 1984, 22, 1041; see also Gaskell, A. J.; Joule, J. A. Tetrahedron 1967, 23, 4053. Sakai, S.; Ogawa, M. Heterocycles 1978, 10, 67.
31. For the total synthesis of deserpidine see (a) Szantay, C.; Blaskó, G.; Honty, K.; Baitz-Gacs, E.; Toke, L. Liebigs Ann. Chem. 1983, 1292. (b) Miyata, O.; Hirata, Y.; Naito, T.; Ninomiya, I. Heterocycles 1984, 22, 1041; see also Gaskell, A. J.; Joule, J. A. Tetrahedron 1967, 23, 4053. Sakai, S.; Ogawa, M. Heterocycles 1978, 10, 67.
32. For the total synthesis of deserpidine see (a) Szantay, C.; Blaskó, G.; Honty, K.; Baitz-Gacs, E.; Toke, L. Liebigs Ann. Chem. 1983, 1292. (b) Miyata, O.; Hirata, Y.; Naito, T.; Ninomiya, I. Heterocycles 1984, 22, 1041; see also Gaskell, A. J.; Joule, J. A. Tetrahedron 1967, 23, 4053. Sakai, S.; Ogawa, M. Heterocycles 1978, 10, 67.
33. (a) Van Tamelen, E. E.; Shamma, M.; Burgstahler, A. W.; Wolinsky, J.; Tamm, R.; Aldrich, P. E. J. Am. Chem. Soc. 1969, 91, 7315.
34. (b) Toke, L.; Honty, K.; Szantay, C.Chem. Ber. 1969, 102, 3248.
35. (c) Stork, G.; Guthikonda, R. N. J. Am. Chem. Soc. 1972, 94, 5109.
36. (d) Kametani, T.; Hirai, Y.; Fukumoto, K. Chem. Pharm. Bull. Jpn. 1976, 24, 2500.
37. (e) Szantay, C.; Honty, K.; Toke, L; Szabo, L. Chem. Ber. 1976, 109, 1737.
38. (f) Wenkert, E.; Chang, C.-J.; Chawla, H. P. S.; Cochran, D. W.; Hagaman, E.W.; King, J. C.; Orito, K. J. Am. Chem. Soc. 1976, 98, 3645.
39. (g) Wenkert, E.; Halls, T. D. J.; Kunesch, G.; Orito, K.; Stephens, R. L.; Temple, W. A.; Yadav, J. S. J. Am. Chem. Soc. 1979, 101, 5370.
40. (h) Kametani, T.; Suzuki, T.; Unno, K. Tetrahedron 1981, 37, 3819.
41. (i) Wenkert, E.; Pyrek, J.St.; Uesato, S.; Vankar, Y. D. J. Am. Chem. Soc. 1982, 104, 2244.
42. (j) Miyata, O.; Hirata, Y.; Naito, T.; Ninomiya, I. J. Chem. Soc., Chem. Commun. 1983, 1231.
43. (k) Danishefsky, S.; Langer, M. E.; Vogel, C. Tetrahedron Lett. 1985, 26, 5983.
44. (1) Blaskó, G.; Knight, H.; Honty, K.; Szantay, C. Liebigs Ann. Chem. 1986, 655.
45. (m) Toke, L.; Honty, K.; Szabo, L.; Blasko, G.; Szantay, C. J. Org. Chem. 1973, 38, 2496.
46. (n) Aube, J.; Ghosh, S.; Tanol, M. J. Am. Chem. Soc. 1994, 116, 9009.
47. (o) Stork, G.; Hill, R. K. J. Am. Chem. Soc. 1957, 79, 495.
48. (p) Lounasmaa, M.; Jokela, R. Tetrahedron Lett. 1990, 46, 615.
49. Hanessian, S. in Total Synthesis of Natural Products: The "Chiron" Approach; Baldwin, J. E., Ed., Pergamon: Oxford, 1983.
50. For selected examples of the use of (-)-quinic acid as a starting material and a chiral template in total synthesis since 1989, see (a) Ulibarri, G.; Audrain, H.; Nadler, W.; Lhermitt, H.; Grierson, D. S. Pure Appl. Chem. 1996, 68, 601. (b) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Synlett 1996, 29. (c) White, J. D.; Cammack, J. H.; Sakuma, K.; Rewcastle, G. W.; Widener, R. K. J. Org. Chem. 1995, 60, 3600. (d) Kamenecka, T.; Overman, L. E. Tetrahedron Lett. 1994, 25, 4279. (e) Barros, M. T.; Santos, A. G.; Godinho, L. S.; Maycock, C. D. Tetrahedron Lett. 1994, 23, 3999. (f) Frost, J. W., Montchamp, J. L. J. Org. Chem. 1994, 59, 7596. (g) Huang, P. Q.; Sabbe, K.; Pottie, M.; Vandewalle, M. Tetrahedron Lett. 1995, 36, 8299. (h) McComsey, D. F.; Maryanoff, B. E. J. Org. Chem. 1994, 59, 2652. (i) Shing, T. K. M.; Wan, L. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1643. (j) Mills, S.; Desmond, R.; Reamer, R. A.; Volante, R. P.; Shinkai, I. Tetrahedron Lett. 1988, 29, 281, (k) Maycock, C. D.; Barros, M. T.; Santos, A. G.; Godinho, L. S. Tetrahedron Lett. 1992, 33, 4633. (1) Su, Z.; Paquette, L. A. J. Org. Chem. 1995, 60, 764. (m) White, J. M.; Toske, S. G.; Yakura, T. Synlett 1994, 591 (n) Hanessian, S.; Sakito, Y.; Dhanoa, D.; Baptistella, L. Tetrahedron 1989, 45, 6623.
51. For selected examples of the use of (-)-quinic acid as a starting material and a chiral template in total synthesis since 1989, see (a) Ulibarri, G.; Audrain, H.; Nadler, W.; Lhermitt, H.; Grierson, D. S. Pure Appl. Chem. 1996, 68, 601. (b) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Synlett 1996, 29. (c) White, J. D.; Cammack, J. H.; Sakuma, K.; Rewcastle, G. W.; Widener, R. K. J. Org. Chem. 1995, 60, 3600. (d) Kamenecka, T.; Overman, L. E. Tetrahedron Lett. 1994, 25, 4279. (e) Barros, M. T.; Santos, A. G.; Godinho, L. S.; Maycock, C. D. Tetrahedron Lett. 1994, 23, 3999. (f) Frost, J. W., Montchamp, J. L. J. Org. Chem. 1994, 59, 7596. (g) Huang, P. Q.; Sabbe, K.; Pottie, M.; Vandewalle, M. Tetrahedron Lett. 1995, 36, 8299. (h) McComsey, D. F.; Maryanoff, B. E. J. Org. Chem. 1994, 59, 2652. (i) Shing, T. K. M.; Wan, L. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1643. (j) Mills, S.; Desmond, R.; Reamer, R. A.; Volante, R. P.; Shinkai, I. Tetrahedron Lett. 1988, 29, 281, (k) Maycock, C. D.; Barros, M. T.; Santos, A. G.; Godinho, L. S. Tetrahedron Lett. 1992, 33, 4633. (1) Su, Z.; Paquette, L. A. J. Org. Chem. 1995, 60, 764. (m) White, J. M.; Toske, S. G.; Yakura, T. Synlett 1994, 591 (n) Hanessian, S.; Sakito, Y.; Dhanoa, D.; Baptistella, L. Tetrahedron 1989, 45, 6623.
52. For selected examples of the use of (-)-quinic acid as a starting material and a chiral template in total synthesis since 1989, see (a) Ulibarri, G.; Audrain, H.; Nadler, W.; Lhermitt, H.; Grierson, D. S. Pure Appl. Chem. 1996, 68, 601. (b) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Synlett 1996, 29. (c) White, J. D.; Cammack, J. H.; Sakuma, K.; Rewcastle, G. W.; Widener, R. K. J. Org. Chem. 1995, 60, 3600. (d) Kamenecka, T.; Overman, L. E. Tetrahedron Lett. 1994, 25, 4279. (e) Barros, M. T.; Santos, A. G.; Godinho, L. S.; Maycock, C. D. Tetrahedron Lett. 1994, 23, 3999. (f) Frost, J. W., Montchamp, J. L. J. Org. Chem. 1994, 59, 7596. (g) Huang, P. Q.; Sabbe, K.; Pottie, M.; Vandewalle, M. Tetrahedron Lett. 1995, 36, 8299. (h) McComsey, D. F.; Maryanoff, B. E. J. Org. Chem. 1994, 59, 2652. (i) Shing, T. K. M.; Wan, L. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1643. (j) Mills, S.; Desmond, R.; Reamer, R. A.; Volante, R. P.; Shinkai, I. Tetrahedron Lett. 1988, 29, 281, (k) Maycock, C. D.; Barros, M. T.; Santos, A. G.; Godinho, L. S. Tetrahedron Lett. 1992, 33, 4633. (1) Su, Z.; Paquette, L. A. J. Org. Chem. 1995, 60, 764. (m) White, J. M.; Toske, S. G.; Yakura, T. Synlett 1994, 591 (n) Hanessian, S.; Sakito, Y.; Dhanoa, D.; Baptistella, L. Tetrahedron 1989, 45, 6623.
53. For selected examples of the use of (-)-quinic acid as a starting material and a chiral template in total synthesis since 1989, see (a) Ulibarri, G.; Audrain, H.; Nadler, W.; Lhermitt, H.; Grierson, D. S. Pure Appl. Chem. 1996, 68, 601. (b) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Synlett 1996, 29. (c) White, J. D.; Cammack, J. H.; Sakuma, K.; Rewcastle, G. W.; Widener, R. K. J. Org. Chem. 1995, 60, 3600. (d) Kamenecka, T.; Overman, L. E. Tetrahedron Lett. 1994, 25, 4279. (e) Barros, M. T.; Santos, A. G.; Godinho, L. S.; Maycock, C. D. Tetrahedron Lett. 1994, 23, 3999. (f) Frost, J. W., Montchamp, J. L. J. Org. Chem. 1994, 59, 7596. (g) Huang, P. Q.; Sabbe, K.; Pottie, M.; Vandewalle, M. Tetrahedron Lett. 1995, 36, 8299. (h) McComsey, D. F.; Maryanoff, B. E. J. Org. Chem. 1994, 59, 2652. (i) Shing, T. K. M.; Wan, L. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1643. (j) Mills, S.; Desmond, R.; Reamer, R. A.; Volante, R. P.; Shinkai, I. Tetrahedron Lett. 1988, 29, 281, (k) Maycock, C. D.; Barros, M. T.; Santos, A. G.; Godinho, L. S. Tetrahedron Lett. 1992, 33, 4633. (1) Su, Z.; Paquette, L. A. J. Org. Chem. 1995, 60, 764. (m) White, J. M.; Toske, S. G.; Yakura, T. Synlett 1994, 591 (n) Hanessian, S.; Sakito, Y.; Dhanoa, D.; Baptistella, L. Tetrahedron 1989, 45, 6623.
54. For selected examples of the use of (-)-quinic acid as a starting material and a chiral template in total synthesis since 1989, see (a) Ulibarri, G.; Audrain, H.; Nadler, W.; Lhermitt, H.; Grierson, D. S. Pure Appl. Chem. 1996, 68, 601. (b) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Synlett 1996, 29. (c) White, J. D.; Cammack, J. H.; Sakuma, K.; Rewcastle, G. W.; Widener, R. K. J. Org. Chem. 1995, 60, 3600. (d) Kamenecka, T.; Overman, L. E. Tetrahedron Lett. 1994, 25, 4279. (e) Barros, M. T.; Santos, A. G.; Godinho, L. S.; Maycock, C. D. Tetrahedron Lett. 1994, 23, 3999. (f) Frost, J. W., Montchamp, J. L. J. Org. Chem. 1994, 59, 7596. (g) Huang, P. Q.; Sabbe, K.; Pottie, M.; Vandewalle, M. Tetrahedron Lett. 1995, 36, 8299. (h) McComsey, D. F.; Maryanoff, B. E. J. Org. Chem. 1994, 59, 2652. (i) Shing, T. K. M.; Wan, L. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1643. (j) Mills, S.; Desmond, R.; Reamer, R. A.; Volante, R. P.; Shinkai, I. Tetrahedron Lett. 1988, 29, 281, (k) Maycock, C. D.; Barros, M. T.; Santos, A. G.; Godinho, L. S. Tetrahedron Lett. 1992, 33, 4633. (1) Su, Z.; Paquette, L. A. J. Org. Chem. 1995, 60, 764. (m) White, J. M.; Toske, S. G.; Yakura, T. Synlett 1994, 591 (n) Hanessian, S.; Sakito, Y.; Dhanoa, D.; Baptistella, L. Tetrahedron 1989, 45, 6623.
55. For selected examples of the use of (-)-quinic acid as a starting material and a chiral template in total synthesis since 1989, see (a) Ulibarri, G.; Audrain, H.; Nadler, W.; Lhermitt, H.; Grierson, D. S. Pure Appl. Chem. 1996, 68, 601. (b) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Synlett 1996, 29. (c) White, J. D.; Cammack, J. H.; Sakuma, K.; Rewcastle, G. W.; Widener, R. K. J. Org. Chem. 1995, 60, 3600. (d) Kamenecka, T.; Overman, L. E. Tetrahedron Lett. 1994, 25, 4279. (e) Barros, M. T.; Santos, A. G.; Godinho, L. S.; Maycock, C. D. Tetrahedron Lett. 1994, 23, 3999. (f) Frost, J. W., Montchamp, J. L. J. Org. Chem. 1994, 59, 7596. (g) Huang, P. Q.; Sabbe, K.; Pottie, M.; Vandewalle, M. Tetrahedron Lett. 1995, 36, 8299. (h) McComsey, D. F.; Maryanoff, B. E. J. Org. Chem. 1994, 59, 2652. (i) Shing, T. K. M.; Wan, L. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1643. (j) Mills, S.; Desmond, R.; Reamer, R. A.; Volante, R. P.; Shinkai, I. Tetrahedron Lett. 1988, 29, 281, (k) Maycock, C. D.; Barros, M. T.; Santos, A. G.; Godinho, L. S. Tetrahedron Lett. 1992, 33, 4633. (1) Su, Z.; Paquette, L. A. J. Org. Chem. 1995, 60, 764. (m) White, J. M.; Toske, S. G.; Yakura, T. Synlett 1994, 591 (n) Hanessian, S.; Sakito, Y.; Dhanoa, D.; Baptistella, L. Tetrahedron 1989, 45, 6623.
56. For selected examples of the use of (-)-quinic acid as a starting material and a chiral template in total synthesis since 1989, see (a) Ulibarri, G.; Audrain, H.; Nadler, W.; Lhermitt, H.; Grierson, D. S. Pure Appl. Chem. 1996, 68, 601. (b) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Synlett 1996, 29. (c) White, J. D.; Cammack, J. H.; Sakuma, K.; Rewcastle, G. W.; Widener, R. K. J. Org. Chem. 1995, 60, 3600. (d) Kamenecka, T.; Overman, L. E. Tetrahedron Lett. 1994, 25, 4279. (e) Barros, M. T.; Santos, A. G.; Godinho, L. S.; Maycock, C. D. Tetrahedron Lett. 1994, 23, 3999. (f) Frost, J. W., Montchamp, J. L. J. Org. Chem. 1994, 59, 7596. (g) Huang, P. Q.; Sabbe, K.; Pottie, M.; Vandewalle, M. Tetrahedron Lett. 1995, 36, 8299. (h) McComsey, D. F.; Maryanoff, B. E. J. Org. Chem. 1994, 59, 2652. (i) Shing, T. K. M.; Wan, L. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1643. (j) Mills, S.; Desmond, R.; Reamer, R. A.; Volante, R. P.; Shinkai, I. Tetrahedron Lett. 1988, 29, 281, (k) Maycock, C. D.; Barros, M. T.; Santos, A. G.; Godinho, L. S. Tetrahedron Lett. 1992, 33, 4633. (1) Su, Z.; Paquette, L. A. J. Org. Chem. 1995, 60, 764. (m) White, J. M.; Toske, S. G.; Yakura, T. Synlett 1994, 591 (n) Hanessian, S.; Sakito, Y.; Dhanoa, D.; Baptistella, L. Tetrahedron 1989, 45, 6623.
57. For selected examples of the use of (-)-quinic acid as a starting material and a chiral template in total synthesis since 1989, see (a) Ulibarri, G.; Audrain, H.; Nadler, W.; Lhermitt, H.; Grierson, D. S. Pure Appl. Chem. 1996, 68, 601. (b) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Synlett 1996, 29. (c) White, J. D.; Cammack, J. H.; Sakuma, K.; Rewcastle, G. W.; Widener, R. K. J. Org. Chem. 1995, 60, 3600. (d) Kamenecka, T.; Overman, L. E. Tetrahedron Lett. 1994, 25, 4279. (e) Barros, M. T.; Santos, A. G.; Godinho, L. S.; Maycock, C. D. Tetrahedron Lett. 1994, 23, 3999. (f) Frost, J. W., Montchamp, J. L. J. Org. Chem. 1994, 59, 7596. (g) Huang, P. Q.; Sabbe, K.; Pottie, M.; Vandewalle, M. Tetrahedron Lett. 1995, 36, 8299. (h) McComsey, D. F.; Maryanoff, B. E. J. Org. Chem. 1994, 59, 2652. (i) Shing, T. K. M.; Wan, L. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1643. (j) Mills, S.; Desmond, R.; Reamer, R. A.; Volante, R. P.; Shinkai, I. Tetrahedron Lett. 1988, 29, 281, (k) Maycock, C. D.; Barros, M. T.; Santos, A. G.; Godinho, L. S. Tetrahedron Lett. 1992, 33, 4633. (1) Su, Z.; Paquette, L. A. J. Org. Chem. 1995, 60, 764. (m) White, J. M.; Toske, S. G.; Yakura, T. Synlett 1994, 591 (n) Hanessian, S.; Sakito, Y.; Dhanoa, D.; Baptistella, L. Tetrahedron 1989, 45, 6623.
58. For selected examples of the use of (-)-quinic acid as a starting material and a chiral template in total synthesis since 1989, see (a) Ulibarri, G.; Audrain, H.; Nadler, W.; Lhermitt, H.; Grierson, D. S. Pure Appl. Chem. 1996, 68, 601. (b) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Synlett 1996, 29. (c) White, J. D.; Cammack, J. H.; Sakuma, K.; Rewcastle, G. W.; Widener, R. K. J. Org. Chem. 1995, 60, 3600. (d) Kamenecka, T.; Overman, L. E. Tetrahedron Lett. 1994, 25, 4279. (e) Barros, M. T.; Santos, A. G.; Godinho, L. S.; Maycock, C. D. Tetrahedron Lett. 1994, 23, 3999. (f) Frost, J. W., Montchamp, J. L. J. Org. Chem. 1994, 59, 7596. (g) Huang, P. Q.; Sabbe, K.; Pottie, M.; Vandewalle, M. Tetrahedron Lett. 1995, 36, 8299. (h) McComsey, D. F.; Maryanoff, B. E. J. Org. Chem. 1994, 59, 2652. (i) Shing, T. K. M.; Wan, L. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1643. (j) Mills, S.; Desmond, R.; Reamer, R. A.; Volante, R. P.; Shinkai, I. Tetrahedron Lett. 1988, 29, 281, (k) Maycock, C. D.; Barros, M. T.; Santos, A. G.; Godinho, L. S. Tetrahedron Lett. 1992, 33, 4633. (1) Su, Z.; Paquette, L. A. J. Org. Chem. 1995, 60, 764. (m) White, J. M.; Toske, S. G.; Yakura, T. Synlett 1994, 591 (n) Hanessian, S.; Sakito, Y.; Dhanoa, D.; Baptistella, L. Tetrahedron 1989, 45, 6623.
59. For selected examples of the use of (-)-quinic acid as a starting material and a chiral template in total synthesis since 1989, see (a) Ulibarri, G.; Audrain, H.; Nadler, W.; Lhermitt, H.; Grierson, D. S. Pure Appl. Chem. 1996, 68, 601. (b) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Synlett 1996, 29. (c) White, J. D.; Cammack, J. H.; Sakuma, K.; Rewcastle, G. W.; Widener, R. K. J. Org. Chem. 1995, 60, 3600. (d) Kamenecka, T.; Overman, L. E. Tetrahedron Lett. 1994, 25, 4279. (e) Barros, M. T.; Santos, A. G.; Godinho, L. S.; Maycock, C. D. Tetrahedron Lett. 1994, 23, 3999. (f) Frost, J. W., Montchamp, J. L. J. Org. Chem. 1994, 59, 7596. (g) Huang, P. Q.; Sabbe, K.; Pottie, M.; Vandewalle, M. Tetrahedron Lett. 1995, 36, 8299. (h) McComsey, D. F.; Maryanoff, B. E. J. Org. Chem. 1994, 59, 2652. (i) Shing, T. K. M.; Wan, L. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1643. (j) Mills, S.; Desmond, R.; Reamer, R. A.; Volante, R. P.; Shinkai, I. Tetrahedron Lett. 1988, 29, 281, (k) Maycock, C. D.; Barros, M. T.; Santos, A. G.; Godinho, L. S. Tetrahedron Lett. 1992, 33, 4633. (1) Su, Z.; Paquette, L. A. J. Org. Chem. 1995, 60, 764. (m) White, J. M.; Toske, S. G.; Yakura, T. Synlett 1994, 591 (n) Hanessian, S.; Sakito, Y.; Dhanoa, D.; Baptistella, L. Tetrahedron 1989, 45, 6623.
60. For selected examples of the use of (-)-quinic acid as a starting material and a chiral template in total synthesis since 1989, see (a) Ulibarri, G.; Audrain, H.; Nadler, W.; Lhermitt, H.; Grierson, D. S. Pure Appl. Chem. 1996, 68, 601. (b) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Synlett 1996, 29. (c) White, J. D.; Cammack, J. H.; Sakuma, K.; Rewcastle, G. W.; Widener, R. K. J. Org. Chem. 1995, 60, 3600. (d) Kamenecka, T.; Overman, L. E. Tetrahedron Lett. 1994, 25, 4279. (e) Barros, M. T.; Santos, A. G.; Godinho, L. S.; Maycock, C. D. Tetrahedron Lett. 1994, 23, 3999. (f) Frost, J. W., Montchamp, J. L. J. Org. Chem. 1994, 59, 7596. (g) Huang, P. Q.; Sabbe, K.; Pottie, M.; Vandewalle, M. Tetrahedron Lett. 1995, 36, 8299. (h) McComsey, D. F.; Maryanoff, B. E. J. Org. Chem. 1994, 59, 2652. (i) Shing, T. K. M.; Wan, L. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1643. (j) Mills, S.; Desmond, R.; Reamer, R. A.; Volante, R. P.; Shinkai, I. Tetrahedron Lett. 1988, 29, 281, (k) Maycock, C. D.; Barros, M. T.; Santos, A. G.; Godinho, L. S. Tetrahedron Lett. 1992, 33, 4633. (1) Su, Z.; Paquette, L. A. J. Org. Chem. 1995, 60, 764. (m) White, J. M.; Toske, S. G.; Yakura, T. Synlett 1994, 591 (n) Hanessian, S.; Sakito, Y.; Dhanoa, D.; Baptistella, L. Tetrahedron 1989, 45, 6623.
61. For selected examples of the use of (-)-quinic acid as a starting material and a chiral template in total synthesis since 1989, see (a) Ulibarri, G.; Audrain, H.; Nadler, W.; Lhermitt, H.; Grierson, D. S. Pure Appl. Chem. 1996, 68, 601. (b) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Synlett 1996, 29. (c) White, J. D.; Cammack, J. H.; Sakuma, K.; Rewcastle, G. W.; Widener, R. K. J. Org. Chem. 1995, 60, 3600. (d) Kamenecka, T.; Overman, L. E. Tetrahedron Lett. 1994, 25, 4279. (e) Barros, M. T.; Santos, A. G.; Godinho, L. S.; Maycock, C. D. Tetrahedron Lett. 1994, 23, 3999. (f) Frost, J. W., Montchamp, J. L. J. Org. Chem. 1994, 59, 7596. (g) Huang, P. Q.; Sabbe, K.; Pottie, M.; Vandewalle, M. Tetrahedron Lett. 1995, 36, 8299. (h) McComsey, D. F.; Maryanoff, B. E. J. Org. Chem. 1994, 59, 2652. (i) Shing, T. K. M.; Wan, L. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1643. (j) Mills, S.; Desmond, R.; Reamer, R. A.; Volante, R. P.; Shinkai, I. Tetrahedron Lett. 1988, 29, 281, (k) Maycock, C. D.; Barros, M. T.; Santos, A. G.; Godinho, L. S. Tetrahedron Lett. 1992, 33, 4633. (1) Su, Z.; Paquette, L. A. J. Org. Chem. 1995, 60, 764. (m) White, J. M.; Toske, S. G.; Yakura, T. Synlett 1994, 591 (n) Hanessian, S.; Sakito, Y.; Dhanoa, D.; Baptistella, L. Tetrahedron 1989, 45, 6623.
62. For selected examples of the use of (-)-quinic acid as a starting material and a chiral template in total synthesis since 1989, see (a) Ulibarri, G.; Audrain, H.; Nadler, W.; Lhermitt, H.; Grierson, D. S. Pure Appl. Chem. 1996, 68, 601. (b) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Synlett 1996, 29. (c) White, J. D.; Cammack, J. H.; Sakuma, K.; Rewcastle, G. W.; Widener, R. K. J. Org. Chem. 1995, 60, 3600. (d) Kamenecka, T.; Overman, L. E. Tetrahedron Lett. 1994, 25, 4279. (e) Barros, M. T.; Santos, A. G.; Godinho, L. S.; Maycock, C. D. Tetrahedron Lett. 1994, 23, 3999. (f) Frost, J. W., Montchamp, J. L. J. Org. Chem. 1994, 59, 7596. (g) Huang, P. Q.; Sabbe, K.; Pottie, M.; Vandewalle, M. Tetrahedron Lett. 1995, 36, 8299. (h) McComsey, D. F.; Maryanoff, B. E. J. Org. Chem. 1994, 59, 2652. (i) Shing, T. K. M.; Wan, L. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1643. (j) Mills, S.; Desmond, R.; Reamer, R. A.; Volante, R. P.; Shinkai, I. Tetrahedron Lett. 1988, 29, 281, (k) Maycock, C. D.; Barros, M. T.; Santos, A. G.; Godinho, L. S. Tetrahedron Lett. 1992, 33, 4633. (1) Su, Z.; Paquette, L. A. J. Org. Chem. 1995, 60, 764. (m) White, J. M.; Toske, S. G.; Yakura, T. Synlett 1994, 591 (n) Hanessian, S.; Sakito, Y.; Dhanoa, D.; Baptistella, L. Tetrahedron 1989, 45, 6623.
63. For selected examples of the use of (-)-quinic acid as a starting material and a chiral template in total synthesis since 1989, see (a) Ulibarri, G.; Audrain, H.; Nadler, W.; Lhermitt, H.; Grierson, D. S. Pure Appl. Chem. 1996, 68, 601. (b) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Synlett 1996, 29. (c) White, J. D.; Cammack, J. H.; Sakuma, K.; Rewcastle, G. W.; Widener, R. K. J. Org. Chem. 1995, 60, 3600. (d) Kamenecka, T.; Overman, L. E. Tetrahedron Lett. 1994, 25, 4279. (e) Barros, M. T.; Santos, A. G.; Godinho, L. S.; Maycock, C. D. Tetrahedron Lett. 1994, 23, 3999. (f) Frost, J. W., Montchamp, J. L. J. Org. Chem. 1994, 59, 7596. (g) Huang, P. Q.; Sabbe, K.; Pottie, M.; Vandewalle, M. Tetrahedron Lett. 1995, 36, 8299. (h) McComsey, D. F.; Maryanoff, B. E. J. Org. Chem. 1994, 59, 2652. (i) Shing, T. K. M.; Wan, L. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1643. (j) Mills, S.; Desmond, R.; Reamer, R. A.; Volante, R. P.; Shinkai, I. Tetrahedron Lett. 1988, 29, 281, (k) Maycock, C. D.; Barros, M. T.; Santos, A. G.; Godinho, L. S. Tetrahedron Lett. 1992, 33, 4633. (1) Su, Z.; Paquette, L. A. J. Org. Chem. 1995, 60, 764. (m) White, J. M.; Toske, S. G.; Yakura, T. Synlett 1994, 591 (n) Hanessian, S.; Sakito, Y.; Dhanoa, D.; Baptistella, L. Tetrahedron 1989, 45, 6623.
64. Philippe, M.; Sepulchre, A. M.; Gero, S. D.; Loibner, H.; Streicher, W.; Stutz, P. J. Antibiotics 1982, 35, 1507.
65. (a) Roush, W. R.; Michaelides, M. R.; Tai, D. F.; Lesur, B. M.; Chong, W. K. M.; Harris, D. J. J. Am. Chem. Soc. 1989, 111, 2984.
66. (b) Bliard, C.; Herczegh, P.; Olesker, A.; Lukacs, G. J. Carbohydr. Chem. 1989, 8, 103.
67. (c) David, S.; Hanessian, S. Tetrahedron 1985, 41, 643.
68. Pearlman, W, M. Tetrahedron Lett. 1967, 1663.
69. Hanessian, S.; DiFabio, R.; Prud'Homme, M.; Marcoux, J.-F. J. Org. Chem. 1990, 55, 3436. See also (a) Nagai, Y.; Matsumoto, H.; Kayama, M.; Nakano, T. Chemistry Lett. 1981, 415. (b) Kraus, G. A.; Landgrebe, K. Tetrahedron Lett. 1984, 25, 3939. (c) Belletire, J. L.; Mahmoodi, N. O. Tetrahedron Lett. 1989, 30, 4363. (d) Curran, D. P.; Chang, C. T. J. Org. Chem. 1989, 54, 3140.
70. Hanessian, S.; DiFabio, R.; Prud'Homme, M.; Marcoux, J.-F. J. Org. Chem. 1990, 55, 3436. See also (a) Nagai, Y.; Matsumoto, H.; Kayama, M.; Nakano, T. Chemistry Lett. 1981, 415. (b) Kraus, G. A.; Landgrebe, K. Tetrahedron Lett. 1984, 25, 3939. (c) Belletire, J. L.; Mahmoodi, N. O. Tetrahedron Lett. 1989, 30, 4363. (d) Curran, D. P.; Chang, C. T. J. Org. Chem. 1989, 54, 3140.
71. Hanessian, S.; DiFabio, R.; Prud'Homme, M.; Marcoux, J.-F. J. Org. Chem. 1990, 55, 3436. See also (a) Nagai, Y.; Matsumoto, H.; Kayama, M.; Nakano, T. Chemistry Lett. 1981, 415. (b) Kraus, G. A.; Landgrebe, K. Tetrahedron Lett. 1984, 25, 3939. (c) Belletire, J. L.; Mahmoodi, N. O. Tetrahedron Lett. 1989, 30, 4363. (d) Curran, D. P.; Chang, C. T. J. Org. Chem. 1989, 54, 3140.
72. Hanessian, S.; DiFabio, R.; Prud'Homme, M.; Marcoux, J.-F. J. Org. Chem. 1990, 55, 3436. See also (a) Nagai, Y.; Matsumoto, H.; Kayama, M.; Nakano, T. Chemistry Lett. 1981, 415. (b) Kraus, G. A.; Landgrebe, K. Tetrahedron Lett. 1984, 25, 3939. (c) Belletire, J. L.; Mahmoodi, N. O. Tetrahedron Lett. 1989, 30, 4363. (d) Curran, D. P.; Chang, C. T. J. Org. Chem. 1989, 54, 3140.
73. Hanessian, S.; DiFabio, R.; Prud'Homme, M.; Marcoux, J.-F. J. Org. Chem. 1990, 55, 3436. See also (a) Nagai, Y.; Matsumoto, H.; Kayama, M.; Nakano, T. Chemistry Lett. 1981, 415. (b) Kraus, G. A.; Landgrebe, K. Tetrahedron Lett. 1984, 25, 3939. (c) Belletire, J. L.; Mahmoodi, N. O. Tetrahedron Lett. 1989, 30, 4363. (d) Curran, D. P.; Chang, C. T. J. Org. Chem. 1989, 54, 3140.
74. For early examples of ether-directed attack of Grignard reagents, see Wolfrom, M. L.; Hanessian, S. J. Org. Chem. 1962, 27, 1800. See also Still, W. C.; McDonald, J. H. Tetrahedron Lett. 1980, 21, 1031, and references cited therein.
75. For early examples of ether-directed attack of Grignard reagents, see Wolfrom, M. L.; Hanessian, S. J. Org. Chem. 1962, 27, 1800. See also Still, W. C.; McDonald, J. H. Tetrahedron Lett. 1980, 21, 1031, and references cited therein.
76. Surzur, J.-M.; Bertrand, M. P. Pure Appl. Chem. 1988, 60, 1659. See also Stork, G.; Mah, R. Heterocycles 1989, 28, 723.
77. Surzur, J.-M.; Bertrand, M. P. Pure Appl. Chem. 1988, 60, 1659. See also Stork, G.; Mah, R. Heterocycles 1989, 28, 723.
78. (a) Stork, G.; Mook, R. Jr.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741.
79. (b) Ueno, Y.; Chino, K.; Watanabe, M.; Moriya, O.; Okawars, M. J. Am. Chem. Soc. 1982, 104, 5564.
80. Brown, H. C. Boranes in Organic Chemistry; Cornell University Press: Ithaca, New York, 1972.
81. Stork, G. Bull. Chem. Soc. Jpn. 1988, 61, 149.
82. (a) Hanessian, S.; Girard, C.; Chiara, J. L. Tetrahedron Lett. 1992, 33, 573.
83. (b) Girard, C., Ph.D. Thesis, 1994, University of Montreal.
84. Kusuda, K.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1989, 30, 2945.