Synthesis of (-)-bestatin and the Taxotere® side-chain via nitroaldol reaction of (1R)-8-phenylmenthyl glyoxylate

Tetrahedron Letters

Volumn 44, Issue 48, 2003, Pages 8685-8687

  Kudyba, Iwona ^a   Raczko, Jerzy ^a,b   Jurczak, Janusz ^a,c  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

^b INSTITUTE OF PHYSICAL CHEMISTRY   (Poland)

^c UNIVERSITY OF WARSAW   (Poland)

Author keywords

Asymmetric induction; Chiral auxiliary; Nitroalcohols; Nitroaldol reactions

Indexed keywords

1 NITRO 2 PHENYLETHANE; 8 PHENYLMENTHYL GLYOXYLATE; BESTATIN; DOCETAXEL; GLYOXYLIC ACID DERIVATIVE; NITRO DERIVATIVE; PHENYLNITROMETHANE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; COLUMN CHROMATOGRAPHY; DRUG SYNTHESIS; NITROALDOL REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0142184535     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.154     Document Type: Article

References (66)

1. Jauristi E., Quintana D., Escalante J. Aldrichchim. Acta. 27:1994;3-15.
2. Cole D.C. Tetrahedron. 50:1994;9517-9582.
3. Cardillo G., Tomasini C. Chem. Soc. Rev. 25:1996;117-128.
4. Andruszkiewicz R. Pol. J. Chem. 72:1998;1-48. and references cited therein.
5. Babine R.L., Bender S.E. Chem. Rev. 97:1997;1359-1472.
6. Umezawa H., Aoyagi T., Suda H., Hamada M., Takieuchi T. J. Antibiot. 29:1976;97-99. and 100-101.
7. Rubin A.E., Sharpless K.B. Angew. Chem., Int. Ed. Engl. 36:1997;2637-2640.
8. Keding S.J., Dales N.A., Lim S., Beaulieu D., Rich D.H. Synth. Commun. 28:1998;4463-4470.
9. Upadhya T.T., Sudalai A. Tetrahedron: Asymmetry. 8:1997;3685-3689.
10. Bunnage M.E., Davies S.G., Goodwin C.J. J. Chem. Soc., Perkin Trans. 1. 1993;1375-1376.
11. Kato K., Saino T., Nishizawa R., Takita T., Umezawa H. J. Chem. Soc., Perkin Trans. 1. 1980;1618-1621.
12. Nozaki K., Sato N., Takaya H. Tetrahedron: Asymmetry. 4:1993;2179-2182.
13. Patel R.N., Banerjee A., Howell J.M., McNamee C.G., Brzozowski D., Mirfakhrae D., Nanduri V., Thottathil J.K., Szarka L.J. Tetrahedron: Asymmetry. 4:1993;2069-2084.
14. Kearns J., Kayser M.M. Tetrahedron Lett. 35:1994;2845-2848.
15. Wasserman H.H., Xia M., Petersen A.K., Jorgensen M.R., Curtis E.A. Tetrahedron Lett. 40:1999;6163-6166.
16. Herranz R., Castro-Pichel J., Vinnesa S., Garcia Lopez M.T. J. Org. Chem. 55:1990;2232-2234.
17. Matsuda F., Matsumoto T., Ohsaki M., Ito Y., Terashima S. Chem. Lett. 1990;723-724.
18. Denis J.-N., Correa A., Greene A.E. J. Org. Chem. 56:1991;6939-6942.
19. Dondoni A., Perrone D., Semola T. Synthesis. 1995;181-186.
20. Rich D.H., Moon B.J., Boparai A.S. J. Org. Chem. 45:1980;2288-2290.
21. Takemoto Y., Matsumoto T., Ito Y., Terashima S. Tetrahedron Lett. 31:1990;217-218.
22. Manickam G., Nogami H., Kanai M., Gröger H., Shibasaki M. Synlett. 2001;617-620.
23. Hagihara M., Schreiber S.L. J. Am. Chem. Soc. 114:1992;6570-6571.
24. Iwanowicz E.J., Lin J., Roberts D.G.M., Michael I.M., Seiler S.M. Bioorg. Med. Chem. Lett. 2:1992;1607-1612.
25. Matsumoto T., Kobayashi Y., Takemoto Y., Ito Y., Kamijo T., Harada H., Terashima S. Tetrahedron Lett. 31:1990;4175-4176.
26. Cativiela C., Diaz-de-Villegas M.D., Gálvez J.A. Tetrahedron: Asymmetry. 7:1996;529-536.
27. Ha H.-J., Ahn Y.-G., Woo J.-S., Lee G.S., Lee W.K. Bull. Chem. Soc. Jpn. 74:2001;1667-1672.
28. Swindell C.S., Tao M.J. J. Org. Chem. 58:1993;5889-5891.
29. Kobayashi Y., Takemoto Y., Ito S. Tetrahedron Lett. 31:1990;3031-3034.
30. Palomo C., Arrieta A., Cossio F.P., Aizpurua J.M., Mielgo A., Aurrekoetxea N. Tetrahedron Lett. 31:1990;6429-6432.
31. Ito Y., Kamijo T., Harada H., Terashima S. Heterocycles. 30:1990;299-302.
32. Denis J.-N., Greene A.E., Serra A.A., Luche M.-J. J. Org. Chem. 51:1986;46-50.
33. Deng L., Jacobsen E.N. J. Org. Chem. 57:1992;4320-4323.
34. Commerçon A., Bézard D., Bernard F., Bourzat J.D. Tetrahedron Lett. 33:1992;5185-5188.
35. Gou D.-M., Liu Y.-C., Chen C.-S. J. Org. Chem. 58:1993;1287-1289.
36. Bonini C., Righi G.J. J. Chem. Soc. Chem. Commun. 1994;2767-2768.
37. Grosjean F., Huché M., Larchevêque M., Legendre J.J., Petit Y. Tetrahedron. 50:1994;9325-9334.
38. Pastó M., Castejón P., Moyano A., Pericas M.A., Riera A.J. J. Org. Chem. 61:1996;6033-6037.
39. Legters J., Van Dienst E., Lambertus T., Zwanenburg B. Recl. Trav. Chim. Pays-Bas. 111:1992;69-74.
40. Bourzat J.D., Commerçon A. Tetrahedron Lett. 34:1993;6049-6052.
41. Palomo C., Aizpurua J.M., Miranda J.I., Mielgo A., Odriozola J.M. Tetrahedron Lett. 34:1993;6326-6328.
42. Georg G.I., Cheruvallath Z.S., Harriman G.C.B., Hepperle M., Park H. Bioorg. Med. Chem. Lett. 3:1993;2467-2470.
43. Holton R.A., Lin J.H. Bioorg. Med. Chem. Lett. 3:1993;2475-2478.
44. Ojima I., Delaloge F. Chem. Soc. Rev. 26:1997;377-386.
45. Kobayashi S., Osobe T., Ohno M. Tetrahedron Lett. 25:1984;5079-5082.
46. Norman B.H., Morris M.L. Tetrahedron Lett. 33:1992;6803-6806.
47. Jefford C.W., Wang J.B., Lu Z.-H. Tetrahedron Lett. 34:1993;7557-7560.
48. Tsuda M., Muraoka Y., Takeuchi T. J. Antibiot. 49:1996;1031-1035.
49. Kudyba, I. Ph.D. Dissertation, Institute of Organic Chemistry, Polish Academy of Sciences, Warsaw, 2002.
50. For the synthesis of (-)-bestatin, see: (a) Pearson, W. H.; Hines, J. H. J. Org. Chem. 1989, 54, 4235-4237; (b) Palomo, C.; Aizpurua, J. M.; Cuevas, C. J. Chem. Soc., Chem. Commun. 1994, 1957-1958; (c) Koseki, K.; Ebata, T.; Matsushita, H. Biosc. Biotechnol. Biochem. 1996, 60, 534-536; (d) Seki, M.; Nakao, K. Biosc. Biotechnol. Biochem. 1999, 63, 1304-1307; (e) Bergmeier, S. C. ; Stanchina, D. M. J. Org. Chem. 1999, 64, 2852-2859; (f) Semple, J. E.; Owens, T. D.; Nguen, K.; Levy, O. E. Org. Lett. 2000, 2, 2769-2772; (g) Nemoto, H.; Ma, R.; Suzuki, I.; Shibuya, M. Org. Lett. 2000, 2, 4245-4247. See also Refs. 4d and 12a.
51. Whitesell J.K., Bhattacharaya A., Buchanan C.M., Chen H.H., Deyo D., James D., Liu C.-L., Minton M.A. Tetrahedron. 42:1986;2993-3001.
52. Solladié-Cavallo A., Khiar N. Tetrahedron Lett. 29:1988;2189-2192.
53. For the synthesis of Taxotere® side-chain, see: (a) Denis, J.-N.; Correa, A.; Greene, A. E. J. Org. Chem. 1990, 55, 1957-1959; (b) Mukai, C.; Kim, I. J.; Furu, E.; Hanaoka, M. Tetrahedron 1993, 49, 8323-8336; (c) Koskinen, A. M. P.; Karvinen, E. K.; Siirilä, J. P. J. Chem. Soc., Chem. Commun. 1994, 21-22; (d) Bunnage, M. E.; Davies, S. G.; Goodwin, C. J. J. Chem. Soc., Perkin Trans. 1 1994, 2385-2391; (e) Cabon, O.; Buisson, D.; Larchevêque, M.; Azerad, R. Tetrahedron: Asymmetry 1995, 6, 2211-2218; (f) Meunier, N.; Veith, U.; Jäger, V. J. Chem. Soc., Chem. Commun. 1996, 331-332; (g) Pastó, M.; Moyano, A.; Pericas, M. A.; Riera, A. J. Tetrahedron: Asymmetry 1996, 7, 243-262; (h) Hanessian, S.; Sancéau, J.-Y. Can. J. Chem. 1996, 74, 621-624; (i) Bruncko, M.; Schlingloff, G.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1483-1486; (j) Harada, N.; Hashiyama, T.; Ozaki, K.; Yamaguchi, T.; Ando, A.; Tsujihara, K. Heterocycles 1997, 44, 305-318; (k) Merino, P.; Castillo, E.; Franco, S.; Merchán, F. L.; Tejero, T. Tetrahedron 1998, 54, 12301-12322; (l) Ojima, I.; Wang, H.; Wang, T.; Ng, E. W. Tetrahedron Lett. 1998, 39, 923-926; (m) Hamamoto, H.; Mamedov, V. A.; Kitamoto, M.; Hayashi, N.; Tsuboi, S. Tetrahedron: Asymmetry 2000, 11, 4485-4497; (n) Lee, S.-H.; Yoon, J.; Chung, S.-H.; Lee, Y.-S. Tetrahedron 2001, 57, 2139-2145.
54. For the synthesis of Taxotere® side-chain, see: (a) Denis, J.-N.; Correa, A.; Greene, A. E. J. Org. Chem. 1990, 55, 1957-1959; (b) Mukai, C.; Kim, I. J.; Furu, E.; Hanaoka, M. Tetrahedron 1993, 49, 8323-8336; (c) Koskinen, A. M. P.; Karvinen, E. K.; Siirilä, J. P. J. Chem. Soc., Chem. Commun. 1994, 21-22; (d) Bunnage, M. E.; Davies, S. G.; Goodwin, C. J. J. Chem. Soc., Perkin Trans. 1 1994, 2385-2391; (e) Cabon, O.; Buisson, D.; Larchevêque, M.; Azerad, R. Tetrahedron: Asymmetry 1995, 6, 2211-2218; (f) Meunier, N.; Veith, U.; Jäger, V. J. Chem. Soc., Chem. Commun. 1996, 331-332; (g) Pastó, M.; Moyano, A.; Pericas, M. A.; Riera, A. J. Tetrahedron: Asymmetry 1996, 7, 243-262; (h) Hanessian, S.; Sancéau, J.-Y. Can. J. Chem. 1996, 74, 621-624; (i) Bruncko, M.; Schlingloff, G.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1483-1486; (j) Harada, N.; Hashiyama, T.; Ozaki, K.; Yamaguchi, T.; Ando, A.; Tsujihara, K. Heterocycles 1997, 44, 305-318; (k) Merino, P.; Castillo, E.; Franco, S.; Merchán, F. L.; Tejero, T. Tetrahedron 1998, 54, 12301-12322; (l) Ojima, I.; Wang, H.; Wang, T.; Ng, E. W. Tetrahedron Lett. 1998, 39, 923-926; (m) Hamamoto, H.; Mamedov, V. A.; Kitamoto, M.; Hayashi, N.; Tsuboi, S. Tetrahedron: Asymmetry 2000, 11, 4485-4497; (n) Lee, S.-H.; Yoon, J.; Chung, S.-H.; Lee, Y.-S. Tetrahedron 2001, 57, 2139-2145.
55. For the synthesis of Taxotere® side-chain, see: (a) Denis, J.-N.; Correa, A.; Greene, A. E. J. Org. Chem. 1990, 55, 1957-1959; (b) Mukai, C.; Kim, I. J.; Furu, E.; Hanaoka, M. Tetrahedron 1993, 49, 8323-8336; (c) Koskinen, A. M. P.; Karvinen, E. K.; Siirilä, J. P. J. Chem. Soc., Chem. Commun. 1994, 21-22; (d) Bunnage, M. E.; Davies, S. G.; Goodwin, C. J. J. Chem. Soc., Perkin Trans. 1 1994, 2385-2391; (e) Cabon, O.; Buisson, D.; Larchevêque, M.; Azerad, R. Tetrahedron: Asymmetry 1995, 6, 2211-2218; (f) Meunier, N.; Veith, U.; Jäger, V. J. Chem. Soc., Chem. Commun. 1996, 331-332; (g) Pastó, M.; Moyano, A.; Pericas, M. A.; Riera, A. J. Tetrahedron: Asymmetry 1996, 7, 243-262; (h) Hanessian, S.; Sancéau, J.-Y. Can. J. Chem. 1996, 74, 621-624; (i) Bruncko, M.; Schlingloff, G.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1483-1486; (j) Harada, N.; Hashiyama, T.; Ozaki, K.; Yamaguchi, T.; Ando, A.; Tsujihara, K. Heterocycles 1997, 44, 305-318; (k) Merino, P.; Castillo, E.; Franco, S.; Merchán, F. L.; Tejero, T. Tetrahedron 1998, 54, 12301-12322; (l) Ojima, I.; Wang, H.; Wang, T.; Ng, E. W. Tetrahedron Lett. 1998, 39, 923-926; (m) Hamamoto, H.; Mamedov, V. A.; Kitamoto, M.; Hayashi, N.; Tsuboi, S. Tetrahedron: Asymmetry 2000, 11, 4485-4497; (n) Lee, S.-H.; Yoon, J.; Chung, S.-H.; Lee, Y.-S. Tetrahedron 2001, 57, 2139-2145.
56. For the synthesis of Taxotere® side-chain, see: (a) Denis, J.-N.; Correa, A.; Greene, A. E. J. Org. Chem. 1990, 55, 1957-1959; (b) Mukai, C.; Kim, I. J.; Furu, E.; Hanaoka, M. Tetrahedron 1993, 49, 8323-8336; (c) Koskinen, A. M. P.; Karvinen, E. K.; Siirilä, J. P. J. Chem. Soc., Chem. Commun. 1994, 21-22; (d) Bunnage, M. E.; Davies, S. G.; Goodwin, C. J. J. Chem. Soc., Perkin Trans. 1 1994, 2385-2391; (e) Cabon, O.; Buisson, D.; Larchevêque, M.; Azerad, R. Tetrahedron: Asymmetry 1995, 6, 2211-2218; (f) Meunier, N.; Veith, U.; Jäger, V. J. Chem. Soc., Chem. Commun. 1996, 331-332; (g) Pastó, M.; Moyano, A.; Pericas, M. A.; Riera, A. J. Tetrahedron: Asymmetry 1996, 7, 243-262; (h) Hanessian, S.; Sancéau, J.-Y. Can. J. Chem. 1996, 74, 621-624; (i) Bruncko, M.; Schlingloff, G.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1483-1486; (j) Harada, N.; Hashiyama, T.; Ozaki, K.; Yamaguchi, T.; Ando, A.; Tsujihara, K. Heterocycles 1997, 44, 305-318; (k) Merino, P.; Castillo, E.; Franco, S.; Merchán, F. L.; Tejero, T. Tetrahedron 1998, 54, 12301-12322; (l) Ojima, I.; Wang, H.; Wang, T.; Ng, E. W. Tetrahedron Lett. 1998, 39, 923-926; (m) Hamamoto, H.; Mamedov, V. A.; Kitamoto, M.; Hayashi, N.; Tsuboi, S. Tetrahedron: Asymmetry 2000, 11, 4485-4497; (n) Lee, S.-H.; Yoon, J.; Chung, S.-H.; Lee, Y.-S. Tetrahedron 2001, 57, 2139-2145.
57. For the synthesis of Taxotere® side-chain, see: (a) Denis, J.-N.; Correa, A.; Greene, A. E. J. Org. Chem. 1990, 55, 1957-1959; (b) Mukai, C.; Kim, I. J.; Furu, E.; Hanaoka, M. Tetrahedron 1993, 49, 8323-8336; (c) Koskinen, A. M. P.; Karvinen, E. K.; Siirilä, J. P. J. Chem. Soc., Chem. Commun. 1994, 21-22; (d) Bunnage, M. E.; Davies, S. G.; Goodwin, C. J. J. Chem. Soc., Perkin Trans. 1 1994, 2385-2391; (e) Cabon, O.; Buisson, D.; Larchevêque, M.; Azerad, R. Tetrahedron: Asymmetry 1995, 6, 2211-2218; (f) Meunier, N.; Veith, U.; Jäger, V. J. Chem. Soc., Chem. Commun. 1996, 331-332; (g) Pastó, M.; Moyano, A.; Pericas, M. A.; Riera, A. J. Tetrahedron: Asymmetry 1996, 7, 243-262; (h) Hanessian, S.; Sancéau, J.-Y. Can. J. Chem. 1996, 74, 621-624; (i) Bruncko, M.; Schlingloff, G.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1483-1486; (j) Harada, N.; Hashiyama, T.; Ozaki, K.; Yamaguchi, T.; Ando, A.; Tsujihara, K. Heterocycles 1997, 44, 305-318; (k) Merino, P.; Castillo, E.; Franco, S.; Merchán, F. L.; Tejero, T. Tetrahedron 1998, 54, 12301-12322; (l) Ojima, I.; Wang, H.; Wang, T.; Ng, E. W. Tetrahedron Lett. 1998, 39, 923-926; (m) Hamamoto, H.; Mamedov, V. A.; Kitamoto, M.; Hayashi, N.; Tsuboi, S. Tetrahedron: Asymmetry 2000, 11, 4485-4497; (n) Lee, S.-H.; Yoon, J.; Chung, S.-H.; Lee, Y.-S. Tetrahedron 2001, 57, 2139-2145.
58. For the synthesis of Taxotere® side-chain, see: (a) Denis, J.-N.; Correa, A.; Greene, A. E. J. Org. Chem. 1990, 55, 1957-1959; (b) Mukai, C.; Kim, I. J.; Furu, E.; Hanaoka, M. Tetrahedron 1993, 49, 8323-8336; (c) Koskinen, A. M. P.; Karvinen, E. K.; Siirilä, J. P. J. Chem. Soc., Chem. Commun. 1994, 21-22; (d) Bunnage, M. E.; Davies, S. G.; Goodwin, C. J. J. Chem. Soc., Perkin Trans. 1 1994, 2385-2391; (e) Cabon, O.; Buisson, D.; Larchevêque, M.; Azerad, R. Tetrahedron: Asymmetry 1995, 6, 2211-2218; (f) Meunier, N.; Veith, U.; Jäger, V. J. Chem. Soc., Chem. Commun. 1996, 331-332; (g) Pastó, M.; Moyano, A.; Pericas, M. A.; Riera, A. J. Tetrahedron: Asymmetry 1996, 7, 243-262; (h) Hanessian, S.; Sancéau, J.-Y. Can. J. Chem. 1996, 74, 621-624; (i) Bruncko, M.; Schlingloff, G.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1483-1486; (j) Harada, N.; Hashiyama, T.; Ozaki, K.; Yamaguchi, T.; Ando, A.; Tsujihara, K. Heterocycles 1997, 44, 305-318; (k) Merino, P.; Castillo, E.; Franco, S.; Merchán, F. L.; Tejero, T. Tetrahedron 1998, 54, 12301-12322; (l) Ojima, I.; Wang, H.; Wang, T.; Ng, E. W. Tetrahedron Lett. 1998, 39, 923-926; (m) Hamamoto, H.; Mamedov, V. A.; Kitamoto, M.; Hayashi, N.; Tsuboi, S. Tetrahedron: Asymmetry 2000, 11, 4485-4497; (n) Lee, S.-H.; Yoon, J.; Chung, S.-H.; Lee, Y.-S. Tetrahedron 2001, 57, 2139-2145.
59. For the synthesis of Taxotere® side-chain, see: (a) Denis, J.-N.; Correa, A.; Greene, A. E. J. Org. Chem. 1990, 55, 1957-1959; (b) Mukai, C.; Kim, I. J.; Furu, E.; Hanaoka, M. Tetrahedron 1993, 49, 8323-8336; (c) Koskinen, A. M. P.; Karvinen, E. K.; Siirilä, J. P. J. Chem. Soc., Chem. Commun. 1994, 21-22; (d) Bunnage, M. E.; Davies, S. G.; Goodwin, C. J. J. Chem. Soc., Perkin Trans. 1 1994, 2385-2391; (e) Cabon, O.; Buisson, D.; Larchevêque, M.; Azerad, R. Tetrahedron: Asymmetry 1995, 6, 2211-2218; (f) Meunier, N.; Veith, U.; Jäger, V. J. Chem. Soc., Chem. Commun. 1996, 331-332; (g) Pastó, M.; Moyano, A.; Pericas, M. A.; Riera, A. J. Tetrahedron: Asymmetry 1996, 7, 243-262; (h) Hanessian, S.; Sancéau, J.-Y. Can. J. Chem. 1996, 74, 621-624; (i) Bruncko, M.; Schlingloff, G.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1483-1486; (j) Harada, N.; Hashiyama, T.; Ozaki, K.; Yamaguchi, T.; Ando, A.; Tsujihara, K. Heterocycles 1997, 44, 305-318; (k) Merino, P.; Castillo, E.; Franco, S.; Merchán, F. L.; Tejero, T. Tetrahedron 1998, 54, 12301-12322; (l) Ojima, I.; Wang, H.; Wang, T.; Ng, E. W. Tetrahedron Lett. 1998, 39, 923-926; (m) Hamamoto, H.; Mamedov, V. A.; Kitamoto, M.; Hayashi, N.; Tsuboi, S. Tetrahedron: Asymmetry 2000, 11, 4485-4497; (n) Lee, S.-H.; Yoon, J.; Chung, S.-H.; Lee, Y.-S. Tetrahedron 2001, 57, 2139-2145.
60. For the synthesis of Taxotere® side-chain, see: (a) Denis, J.-N.; Correa, A.; Greene, A. E. J. Org. Chem. 1990, 55, 1957-1959; (b) Mukai, C.; Kim, I. J.; Furu, E.; Hanaoka, M. Tetrahedron 1993, 49, 8323-8336; (c) Koskinen, A. M. P.; Karvinen, E. K.; Siirilä, J. P. J. Chem. Soc., Chem. Commun. 1994, 21-22; (d) Bunnage, M. E.; Davies, S. G.; Goodwin, C. J. J. Chem. Soc., Perkin Trans. 1 1994, 2385-2391; (e) Cabon, O.; Buisson, D.; Larchevêque, M.; Azerad, R. Tetrahedron: Asymmetry 1995, 6, 2211-2218; (f) Meunier, N.; Veith, U.; Jäger, V. J. Chem. Soc., Chem. Commun. 1996, 331-332; (g) Pastó, M.; Moyano, A.; Pericas, M. A.; Riera, A. J. Tetrahedron: Asymmetry 1996, 7, 243-262; (h) Hanessian, S.; Sancéau, J.-Y. Can. J. Chem. 1996, 74, 621-624; (i) Bruncko, M.; Schlingloff, G.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1483-1486; (j) Harada, N.; Hashiyama, T.; Ozaki, K.; Yamaguchi, T.; Ando, A.; Tsujihara, K. Heterocycles 1997, 44, 305-318; (k) Merino, P.; Castillo, E.; Franco, S.; Merchán, F. L.; Tejero, T. Tetrahedron 1998, 54, 12301-12322; (l) Ojima, I.; Wang, H.; Wang, T.; Ng, E. W. Tetrahedron Lett. 1998, 39, 923-926; (m) Hamamoto, H.; Mamedov, V. A.; Kitamoto, M.; Hayashi, N.; Tsuboi, S. Tetrahedron: Asymmetry 2000, 11, 4485-4497; (n) Lee, S.-H.; Yoon, J.; Chung, S.-H.; Lee, Y.-S. Tetrahedron 2001, 57, 2139-2145.
61. For the synthesis of Taxotere® side-chain, see: (a) Denis, J.-N.; Correa, A.; Greene, A. E. J. Org. Chem. 1990, 55, 1957-1959; (b) Mukai, C.; Kim, I. J.; Furu, E.; Hanaoka, M. Tetrahedron 1993, 49, 8323-8336; (c) Koskinen, A. M. P.; Karvinen, E. K.; Siirilä, J. P. J. Chem. Soc., Chem. Commun. 1994, 21-22; (d) Bunnage, M. E.; Davies, S. G.; Goodwin, C. J. J. Chem. Soc., Perkin Trans. 1 1994, 2385-2391; (e) Cabon, O.; Buisson, D.; Larchevêque, M.; Azerad, R. Tetrahedron: Asymmetry 1995, 6, 2211-2218; (f) Meunier, N.; Veith, U.; Jäger, V. J. Chem. Soc., Chem. Commun. 1996, 331-332; (g) Pastó, M.; Moyano, A.; Pericas, M. A.; Riera, A. J. Tetrahedron: Asymmetry 1996, 7, 243-262; (h) Hanessian, S.; Sancéau, J.-Y. Can. J. Chem. 1996, 74, 621-624; (i) Bruncko, M.; Schlingloff, G.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1483-1486; (j) Harada, N.; Hashiyama, T.; Ozaki, K.; Yamaguchi, T.; Ando, A.; Tsujihara, K. Heterocycles 1997, 44, 305-318; (k) Merino, P.; Castillo, E.; Franco, S.; Merchán, F. L.; Tejero, T. Tetrahedron 1998, 54, 12301-12322; (l) Ojima, I.; Wang, H.; Wang, T.; Ng, E. W. Tetrahedron Lett. 1998, 39, 923-926; (m) Hamamoto, H.; Mamedov, V. A.; Kitamoto, M.; Hayashi, N.; Tsuboi, S. Tetrahedron: Asymmetry 2000, 11, 4485-4497; (n) Lee, S.-H.; Yoon, J.; Chung, S.-H.; Lee, Y.-S. Tetrahedron 2001, 57, 2139-2145.
62. For the synthesis of Taxotere® side-chain, see: (a) Denis, J.-N.; Correa, A.; Greene, A. E. J. Org. Chem. 1990, 55, 1957-1959; (b) Mukai, C.; Kim, I. J.; Furu, E.; Hanaoka, M. Tetrahedron 1993, 49, 8323-8336; (c) Koskinen, A. M. P.; Karvinen, E. K.; Siirilä, J. P. J. Chem. Soc., Chem. Commun. 1994, 21-22; (d) Bunnage, M. E.; Davies, S. G.; Goodwin, C. J. J. Chem. Soc., Perkin Trans. 1 1994, 2385-2391; (e) Cabon, O.; Buisson, D.; Larchevêque, M.; Azerad, R. Tetrahedron: Asymmetry 1995, 6, 2211-2218; (f) Meunier, N.; Veith, U.; Jäger, V. J. Chem. Soc., Chem. Commun. 1996, 331-332; (g) Pastó, M.; Moyano, A.; Pericas, M. A.; Riera, A. J. Tetrahedron: Asymmetry 1996, 7, 243-262; (h) Hanessian, S.; Sancéau, J.-Y. Can. J. Chem. 1996, 74, 621-624; (i) Bruncko, M.; Schlingloff, G.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1483-1486; (j) Harada, N.; Hashiyama, T.; Ozaki, K.; Yamaguchi, T.; Ando, A.; Tsujihara, K. Heterocycles 1997, 44, 305-318; (k) Merino, P.; Castillo, E.; Franco, S.; Merchán, F. L.; Tejero, T. Tetrahedron 1998, 54, 12301-12322; (l) Ojima, I.; Wang, H.; Wang, T.; Ng, E. W. Tetrahedron Lett. 1998, 39, 923-926; (m) Hamamoto, H.; Mamedov, V. A.; Kitamoto, M.; Hayashi, N.; Tsuboi, S. Tetrahedron: Asymmetry 2000, 11, 4485-4497; (n) Lee, S.-H.; Yoon, J.; Chung, S.-H.; Lee, Y.-S. Tetrahedron 2001, 57, 2139-2145.
63. For the synthesis of Taxotere® side-chain, see: (a) Denis, J.-N.; Correa, A.; Greene, A. E. J. Org. Chem. 1990, 55, 1957-1959; (b) Mukai, C.; Kim, I. J.; Furu, E.; Hanaoka, M. Tetrahedron 1993, 49, 8323-8336; (c) Koskinen, A. M. P.; Karvinen, E. K.; Siirilä, J. P. J. Chem. Soc., Chem. Commun. 1994, 21-22; (d) Bunnage, M. E.; Davies, S. G.; Goodwin, C. J. J. Chem. Soc., Perkin Trans. 1 1994, 2385-2391; (e) Cabon, O.; Buisson, D.; Larchevêque, M.; Azerad, R. Tetrahedron: Asymmetry 1995, 6, 2211-2218; (f) Meunier, N.; Veith, U.; Jäger, V. J. Chem. Soc., Chem. Commun. 1996, 331-332; (g) Pastó, M.; Moyano, A.; Pericas, M. A.; Riera, A. J. Tetrahedron: Asymmetry 1996, 7, 243-262; (h) Hanessian, S.; Sancéau, J.-Y. Can. J. Chem. 1996, 74, 621-624; (i) Bruncko, M.; Schlingloff, G.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1483-1486; (j) Harada, N.; Hashiyama, T.; Ozaki, K.; Yamaguchi, T.; Ando, A.; Tsujihara, K. Heterocycles 1997, 44, 305-318; (k) Merino, P.; Castillo, E.; Franco, S.; Merchán, F. L.; Tejero, T. Tetrahedron 1998, 54, 12301-12322; (l) Ojima, I.; Wang, H.; Wang, T.; Ng, E. W. Tetrahedron Lett. 1998, 39, 923-926; (m) Hamamoto, H.; Mamedov, V. A.; Kitamoto, M.; Hayashi, N.; Tsuboi, S. Tetrahedron: Asymmetry 2000, 11, 4485-4497; (n) Lee, S.-H.; Yoon, J.; Chung, S.-H.; Lee, Y.-S. Tetrahedron 2001, 57, 2139-2145.
64. For the synthesis of Taxotere® side-chain, see: (a) Denis, J.-N.; Correa, A.; Greene, A. E. J. Org. Chem. 1990, 55, 1957-1959; (b) Mukai, C.; Kim, I. J.; Furu, E.; Hanaoka, M. Tetrahedron 1993, 49, 8323-8336; (c) Koskinen, A. M. P.; Karvinen, E. K.; Siirilä, J. P. J. Chem. Soc., Chem. Commun. 1994, 21-22; (d) Bunnage, M. E.; Davies, S. G.; Goodwin, C. J. J. Chem. Soc., Perkin Trans. 1 1994, 2385-2391; (e) Cabon, O.; Buisson, D.; Larchevêque, M.; Azerad, R. Tetrahedron: Asymmetry 1995, 6, 2211-2218; (f) Meunier, N.; Veith, U.; Jäger, V. J. Chem. Soc., Chem. Commun. 1996, 331-332; (g) Pastó, M.; Moyano, A.; Pericas, M. A.; Riera, A. J. Tetrahedron: Asymmetry 1996, 7, 243-262; (h) Hanessian, S.; Sancéau, J.-Y. Can. J. Chem. 1996, 74, 621-624; (i) Bruncko, M.; Schlingloff, G.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1483-1486; (j) Harada, N.; Hashiyama, T.; Ozaki, K.; Yamaguchi, T.; Ando, A.; Tsujihara, K. Heterocycles 1997, 44, 305-318; (k) Merino, P.; Castillo, E.; Franco, S.; Merchán, F. L.; Tejero, T. Tetrahedron 1998, 54, 12301-12322; (l) Ojima, I.; Wang, H.; Wang, T.; Ng, E. W. Tetrahedron Lett. 1998, 39, 923-926; (m) Hamamoto, H.; Mamedov, V. A.; Kitamoto, M.; Hayashi, N.; Tsuboi, S. Tetrahedron: Asymmetry 2000, 11, 4485-4497; (n) Lee, S.-H.; Yoon, J.; Chung, S.-H.; Lee, Y.-S. Tetrahedron 2001, 57, 2139-2145.
65. For the synthesis of Taxotere® side-chain, see: (a) Denis, J.-N.; Correa, A.; Greene, A. E. J. Org. Chem. 1990, 55, 1957-1959; (b) Mukai, C.; Kim, I. J.; Furu, E.; Hanaoka, M. Tetrahedron 1993, 49, 8323-8336; (c) Koskinen, A. M. P.; Karvinen, E. K.; Siirilä, J. P. J. Chem. Soc., Chem. Commun. 1994, 21-22; (d) Bunnage, M. E.; Davies, S. G.; Goodwin, C. J. J. Chem. Soc., Perkin Trans. 1 1994, 2385-2391; (e) Cabon, O.; Buisson, D.; Larchevêque, M.; Azerad, R. Tetrahedron: Asymmetry 1995, 6, 2211-2218; (f) Meunier, N.; Veith, U.; Jäger, V. J. Chem. Soc., Chem. Commun. 1996, 331-332; (g) Pastó, M.; Moyano, A.; Pericas, M. A.; Riera, A. J. Tetrahedron: Asymmetry 1996, 7, 243-262; (h) Hanessian, S.; Sancéau, J.-Y. Can. J. Chem. 1996, 74, 621-624; (i) Bruncko, M.; Schlingloff, G.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1483-1486; (j) Harada, N.; Hashiyama, T.; Ozaki, K.; Yamaguchi, T.; Ando, A.; Tsujihara, K. Heterocycles 1997, 44, 305-318; (k) Merino, P.; Castillo, E.; Franco, S.; Merchán, F. L.; Tejero, T. Tetrahedron 1998, 54, 12301-12322; (l) Ojima, I.; Wang, H.; Wang, T.; Ng, E. W. Tetrahedron Lett. 1998, 39, 923-926; (m) Hamamoto, H.; Mamedov, V. A.; Kitamoto, M.; Hayashi, N.; Tsuboi, S. Tetrahedron: Asymmetry 2000, 11, 4485-4497; (n) Lee, S.-H.; Yoon, J.; Chung, S.-H.; Lee, Y.-S. Tetrahedron 2001, 57, 2139-2145.
66. For the synthesis of Taxotere® side-chain, see: (a) Denis, J.-N.; Correa, A.; Greene, A. E. J. Org. Chem. 1990, 55, 1957-1959; (b) Mukai, C.; Kim, I. J.; Furu, E.; Hanaoka, M. Tetrahedron 1993, 49, 8323-8336; (c) Koskinen, A. M. P.; Karvinen, E. K.; Siirilä, J. P. J. Chem. Soc., Chem. Commun. 1994, 21-22; (d) Bunnage, M. E.; Davies, S. G.; Goodwin, C. J. J. Chem. Soc., Perkin Trans. 1 1994, 2385-2391; (e) Cabon, O.; Buisson, D.; Larchevêque, M.; Azerad, R. Tetrahedron: Asymmetry 1995, 6, 2211-2218; (f) Meunier, N.; Veith, U.; Jäger, V. J. Chem. Soc., Chem. Commun. 1996, 331-332; (g) Pastó, M.; Moyano, A.; Pericas, M. A.; Riera, A. J. Tetrahedron: Asymmetry 1996, 7, 243-262; (h) Hanessian, S.; Sancéau, J.-Y. Can. J. Chem. 1996, 74, 621-624; (i) Bruncko, M.; Schlingloff, G.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1483-1486; (j) Harada, N.; Hashiyama, T.; Ozaki, K.; Yamaguchi, T.; Ando, A.; Tsujihara, K. Heterocycles 1997, 44, 305-318; (k) Merino, P.; Castillo, E.; Franco, S.; Merchán, F. L.; Tejero, T. Tetrahedron 1998, 54, 12301-12322; (l) Ojima, I.; Wang, H.; Wang, T.; Ng, E. W. Tetrahedron Lett. 1998, 39, 923-926; (m) Hamamoto, H.; Mamedov, V. A.; Kitamoto, M.; Hayashi, N.; Tsuboi, S. Tetrahedron: Asymmetry 2000, 11, 4485-4497; (n) Lee, S.-H.; Yoon, J.; Chung, S.-H.; Lee, Y.-S. Tetrahedron 2001, 57, 2139-2145.