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Volumn 7, Issue 1, 1996, Pages 243-262

An enantioselective, stereodivergent approach to anti- and syn-α-hydroxy-β-amino acids from anti-3-amino-1,2-diols. Synthesis of the ready for coupling Taxotere® side chain

Author keywords

[No Author keywords available]

Indexed keywords

3 AMINO 2 HYDROXYPROPIONIC ACID DERIVATIVE; AMINO ACID DERIVATIVE; DOCETAXEL; UNCLASSIFIED DRUG;

EID: 0030031990     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(95)00442-4     Document Type: Article
Times cited : (49)

References (62)
  • 1
    • 0000421507 scopus 로고
    • Compounds with syn configuration: Herranz, R.; Castro-Pichel, J.; García-López, T. Synthesis, 1989, 703. Pearson, W.H.; Hines, J.V.J. Org. Chem. 1989, 54, 4235-4237. Iizuka, K; Kamijo, T.; Harada, H.; Akahane, K.; Kubota, T.; Umeyama, H.; Kiso, Y.J. Chem. Soc. Chem. Commun. 1989, 1678- 1680. Matsumoto, T.; Kobayashi, Y.; Takemoto, Y.; Ito, Y.; Kamijo, T. Harada, H.; Terashima, S.Tetrahedron Lett. 1990, 29, 4175-4176. S. Hoover, D.J.; Damon, D.B. J. Am. Chem. Soc. 1990, 112, 6439. Ojima, I; Park, Y.H.; Sun, C.M.; Brigaud, T.; Zhao, M. Tetrahedron Lett. 1992, 33, 5737-5740. Okino, T.; Matsuda, H.; Murakami, J.Z.; Yamaguchi, K.Tetrahedron Lett. 1993, 34, 501. Jefford, C.W.; Wang, J.B.; Lu, Z.-H. Tetrahedron Lett. 1993, 34, 7557. Wagner, A.; Mollath, M. Tetrahedron Lett. 1993, 34, 619. Yang, L.; Weber, A.E.; Greenlee, W.J.; Patchett, A.A. Tetrahedron Lett. 1993, 34, 7035. Norman, B.H.; Morris, M.L. Tetrahedron Lett. 1992, 33, 6803. Dondoni, A.; Perrone, D. Synthesis, 1993, 1163. Compounds with anti configuration: Yuan, W.; Wong, C.-H.; Haeggström, J.Z.; Wetterholm, A.; Samuelsson, B. J. Am. Chem. Soc. 1992, 114, 6552. Bunnage, M.E.; Davies, S.G.; Goodwin, C.J. Synlett, 1993, 731-732.
    • (1989) Synthesis , pp. 703
    • Herranz, R.1    Castro-Pichel, J.2    García-López, T.3
  • 2
    • 0024450764 scopus 로고
    • Compounds with syn configuration: Herranz, R.; Castro-Pichel, J.; García-López, T. Synthesis, 1989, 703. Pearson, W.H.; Hines, J.V.J. Org. Chem. 1989, 54, 4235-4237. Iizuka, K; Kamijo, T.; Harada, H.; Akahane, K.; Kubota, T.; Umeyama, H.; Kiso, Y.J. Chem. Soc. Chem. Commun. 1989, 1678- 1680. Matsumoto, T.; Kobayashi, Y.; Takemoto, Y.; Ito, Y.; Kamijo, T. Harada, H.; Terashima, S.Tetrahedron Lett. 1990, 29, 4175-4176. S. Hoover, D.J.; Damon, D.B. J. Am. Chem. Soc. 1990, 112, 6439. Ojima, I; Park, Y.H.; Sun, C.M.; Brigaud, T.; Zhao, M. Tetrahedron Lett. 1992, 33, 5737-5740. Okino, T.; Matsuda, H.; Murakami, J.Z.; Yamaguchi, K.Tetrahedron Lett. 1993, 34, 501. Jefford, C.W.; Wang, J.B.; Lu, Z.-H. Tetrahedron Lett. 1993, 34, 7557. Wagner, A.; Mollath, M. Tetrahedron Lett. 1993, 34, 619. Yang, L.; Weber, A.E.; Greenlee, W.J.; Patchett, A.A. Tetrahedron Lett. 1993, 34, 7035. Norman, B.H.; Morris, M.L. Tetrahedron Lett. 1992, 33, 6803. Dondoni, A.; Perrone, D. Synthesis, 1993, 1163. Compounds with anti configuration: Yuan, W.; Wong, C.-H.; Haeggström, J.Z.; Wetterholm, A.; Samuelsson, B. J. Am. Chem. Soc. 1992, 114, 6552. Bunnage, M.E.; Davies, S.G.; Goodwin, C.J. Synlett, 1993, 731-732.
    • (1989) J. Org. Chem. , vol.54 , pp. 4235-4237
    • Pearson, W.H.1    Hines, J.V.2
  • 3
    • 0024438084 scopus 로고
    • Compounds with syn configuration: Herranz, R.; Castro-Pichel, J.; García-López, T. Synthesis, 1989, 703. Pearson, W.H.; Hines, J.V.J. Org. Chem. 1989, 54, 4235-4237. Iizuka, K; Kamijo, T.; Harada, H.; Akahane, K.; Kubota, T.; Umeyama, H.; Kiso, Y.J. Chem. Soc. Chem. Commun. 1989, 1678-1680. Matsumoto, T.; Kobayashi, Y.; Takemoto, Y.; Ito, Y.; Kamijo, T. Harada, H.; Terashima, S.Tetrahedron Lett. 1990, 29, 4175-4176. S. Hoover, D.J.; Damon, D.B. J. Am. Chem. Soc. 1990, 112, 6439. Ojima, I; Park, Y.H.; Sun, C.M.; Brigaud, T.; Zhao, M. Tetrahedron Lett. 1992, 33, 5737-5740. Okino, T.; Matsuda, H.; Murakami, J.Z.; Yamaguchi, K.Tetrahedron Lett. 1993, 34, 501. Jefford, C.W.; Wang, J.B.; Lu, Z.-H. Tetrahedron Lett. 1993, 34, 7557. Wagner, A.; Mollath, M. Tetrahedron Lett. 1993, 34, 619. Yang, L.; Weber, A.E.; Greenlee, W.J.; Patchett, A.A. Tetrahedron Lett. 1993, 34, 7035. Norman, B.H.; Morris, M.L. Tetrahedron Lett. 1992, 33, 6803. Dondoni, A.; Perrone, D. Synthesis, 1993, 1163. Compounds with anti configuration: Yuan, W.; Wong, C.-H.; Haeggström, J.Z.; Wetterholm, A.; Samuelsson, B. J. Am. Chem. Soc. 1992, 114, 6552. Bunnage, M.E.; Davies, S.G.; Goodwin, C.J. Synlett, 1993, 731-732.
    • (1989) J. Chem. Soc. Chem. Commun. , pp. 1678-1680
    • Iizuka, K.1    Kamijo, T.2    Harada, H.3    Akahane, K.4    Kubota, T.5    Umeyama, H.6    Kiso, Y.7
  • 4
    • 0025283995 scopus 로고
    • Compounds with syn configuration: Herranz, R.; Castro-Pichel, J.; García-López, T. Synthesis, 1989, 703. Pearson, W.H.; Hines, J.V.J. Org. Chem. 1989, 54, 4235-4237. Iizuka, K; Kamijo, T.; Harada, H.; Akahane, K.; Kubota, T.; Umeyama, H.; Kiso, Y.J. Chem. Soc. Chem. Commun. 1989, 1678- 1680. Matsumoto, T.; Kobayashi, Y.; Takemoto, Y.; Ito, Y.; Kamijo, T. Harada, H.; Terashima, S.Tetrahedron Lett. 1990, 29, 4175-4176. S. Hoover, D.J.; Damon, D.B. J. Am. Chem. Soc. 1990, 112, 6439. Ojima, I; Park, Y.H.; Sun, C.M.; Brigaud, T.; Zhao, M. Tetrahedron Lett. 1992, 33, 5737-5740. Okino, T.; Matsuda, H.; Murakami, J.Z.; Yamaguchi, K.Tetrahedron Lett. 1993, 34, 501. Jefford, C.W.; Wang, J.B.; Lu, Z.-H. Tetrahedron Lett. 1993, 34, 7557. Wagner, A.; Mollath, M. Tetrahedron Lett. 1993, 34, 619. Yang, L.; Weber, A.E.; Greenlee, W.J.; Patchett, A.A. Tetrahedron Lett. 1993, 34, 7035. Norman, B.H.; Morris, M.L. Tetrahedron Lett. 1992, 33, 6803. Dondoni, A.; Perrone, D. Synthesis, 1993, 1163. Compounds with anti configuration: Yuan, W.; Wong, C.-H.; Haeggström, J.Z.; Wetterholm, A.; Samuelsson, B. J. Am. Chem. Soc. 1992, 114, 6552. Bunnage, M.E.; Davies, S.G.; Goodwin, C.J. Synlett, 1993, 731-732.
    • (1990) Tetrahedron Lett. , vol.29 , pp. 4175-4176
    • Matsumoto, T.1    Kobayashi, Y.2    Takemoto, Y.3    Ito, Y.4    Kamijo, T.5    Harada, H.6    Terashima, S.7
  • 5
    • 0025063399 scopus 로고
    • Compounds with syn configuration: Herranz, R.; Castro-Pichel, J.; García-López, T. Synthesis, 1989, 703. Pearson, W.H.; Hines, J.V.J. Org. Chem. 1989, 54, 4235-4237. Iizuka, K; Kamijo, T.; Harada, H.; Akahane, K.; Kubota, T.; Umeyama, H.; Kiso, Y.J. Chem. Soc. Chem. Commun. 1989, 1678- 1680. Matsumoto, T.; Kobayashi, Y.; Takemoto, Y.; Ito, Y.; Kamijo, T. Harada, H.; Terashima, S.Tetrahedron Lett. 1990, 29, 4175-4176. S. Hoover, D.J.; Damon, D.B. J. Am. Chem. Soc. 1990, 112, 6439. Ojima, I; Park, Y.H.; Sun, C.M.; Brigaud, T.; Zhao, M. Tetrahedron Lett. 1992, 33, 5737-5740. Okino, T.; Matsuda, H.; Murakami, J.Z.; Yamaguchi, K.Tetrahedron Lett. 1993, 34, 501. Jefford, C.W.; Wang, J.B.; Lu, Z.-H. Tetrahedron Lett. 1993, 34, 7557. Wagner, A.; Mollath, M. Tetrahedron Lett. 1993, 34, 619. Yang, L.; Weber, A.E.; Greenlee, W.J.; Patchett, A.A. Tetrahedron Lett. 1993, 34, 7035. Norman, B.H.; Morris, M.L. Tetrahedron Lett. 1992, 33, 6803. Dondoni, A.; Perrone, D. Synthesis, 1993, 1163. Compounds with anti configuration: Yuan, W.; Wong, C.-H.; Haeggström, J.Z.; Wetterholm, A.; Samuelsson, B. J. Am. Chem. Soc. 1992, 114, 6552. Bunnage, M.E.; Davies, S.G.; Goodwin, C.J. Synlett, 1993, 731-732.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 6439
    • Hoover, D.J.S.1    Damon, D.B.2
  • 6
    • 0026774792 scopus 로고
    • Compounds with syn configuration: Herranz, R.; Castro-Pichel, J.; García-López, T. Synthesis, 1989, 703. Pearson, W.H.; Hines, J.V.J. Org. Chem. 1989, 54, 4235-4237. Iizuka, K; Kamijo, T.; Harada, H.; Akahane, K.; Kubota, T.; Umeyama, H.; Kiso, Y.J. Chem. Soc. Chem. Commun. 1989, 1678- 1680. Matsumoto, T.; Kobayashi, Y.; Takemoto, Y.; Ito, Y.; Kamijo, T. Harada, H.; Terashima, S.Tetrahedron Lett. 1990, 29, 4175-4176. S. Hoover, D.J.; Damon, D.B. J. Am. Chem. Soc. 1990, 112, 6439. Ojima, I; Park, Y.H.; Sun, C.M.; Brigaud, T.; Zhao, M. Tetrahedron Lett. 1992, 33, 5737-5740. Okino, T.; Matsuda, H.; Murakami, J.Z.; Yamaguchi, K.Tetrahedron Lett. 1993, 34, 501. Jefford, C.W.; Wang, J.B.; Lu, Z.-H. Tetrahedron Lett. 1993, 34, 7557. Wagner, A.; Mollath, M. Tetrahedron Lett. 1993, 34, 619. Yang, L.; Weber, A.E.; Greenlee, W.J.; Patchett, A.A. Tetrahedron Lett. 1993, 34, 7035. Norman, B.H.; Morris, M.L. Tetrahedron Lett. 1992, 33, 6803. Dondoni, A.; Perrone, D. Synthesis, 1993, 1163. Compounds with anti configuration: Yuan, W.; Wong, C.-H.; Haeggström, J.Z.; Wetterholm, A.; Samuelsson, B. J. Am. Chem. Soc. 1992, 114, 6552. Bunnage, M.E.; Davies, S.G.; Goodwin, C.J. Synlett, 1993, 731-732.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 5737-5740
    • Ojima, I.1    Park, Y.H.2    Sun, C.M.3    Brigaud, T.4    Zhao, M.5
  • 7
    • 0027514449 scopus 로고
    • Compounds with syn configuration: Herranz, R.; Castro-Pichel, J.; García-López, T. Synthesis, 1989, 703. Pearson, W.H.; Hines, J.V.J. Org. Chem. 1989, 54, 4235-4237. Iizuka, K; Kamijo, T.; Harada, H.; Akahane, K.; Kubota, T.; Umeyama, H.; Kiso, Y.J. Chem. Soc. Chem. Commun. 1989, 1678- 1680. Matsumoto, T.; Kobayashi, Y.; Takemoto, Y.; Ito, Y.; Kamijo, T. Harada, H.; Terashima, S.Tetrahedron Lett. 1990, 29, 4175-4176. S. Hoover, D.J.; Damon, D.B. J. Am. Chem. Soc. 1990, 112, 6439. Ojima, I; Park, Y.H.; Sun, C.M.; Brigaud, T.; Zhao, M. Tetrahedron Lett. 1992, 33, 5737-5740. Okino, T.; Matsuda, H.; Murakami, J.Z.; Yamaguchi, K.Tetrahedron Lett. 1993, 34, 501. Jefford, C.W.; Wang, J.B.; Lu, Z.-H. Tetrahedron Lett. 1993, 34, 7557. Wagner, A.; Mollath, M. Tetrahedron Lett. 1993, 34, 619. Yang, L.; Weber, A.E.; Greenlee, W.J.; Patchett, A.A. Tetrahedron Lett. 1993, 34, 7035. Norman, B.H.; Morris, M.L. Tetrahedron Lett. 1992, 33, 6803. Dondoni, A.; Perrone, D. Synthesis, 1993, 1163. Compounds with anti configuration: Yuan, W.; Wong, C.-H.; Haeggström, J.Z.; Wetterholm, A.; Samuelsson, B. J. Am. Chem. Soc. 1992, 114, 6552. Bunnage, M.E.; Davies, S.G.; Goodwin, C.J. Synlett, 1993, 731-732.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 501
    • Okino, T.1    Matsuda, H.2    Murakami, J.Z.3    Yamaguchi, K.4
  • 8
    • 0027491118 scopus 로고
    • Compounds with syn configuration: Herranz, R.; Castro-Pichel, J.; García-López, T. Synthesis, 1989, 703. Pearson, W.H.; Hines, J.V.J. Org. Chem. 1989, 54, 4235-4237. Iizuka, K; Kamijo, T.; Harada, H.; Akahane, K.; Kubota, T.; Umeyama, H.; Kiso, Y.J. Chem. Soc. Chem. Commun. 1989, 1678- 1680. Matsumoto, T.; Kobayashi, Y.; Takemoto, Y.; Ito, Y.; Kamijo, T. Harada, H.; Terashima, S.Tetrahedron Lett. 1990, 29, 4175-4176. S. Hoover, D.J.; Damon, D.B. J. Am. Chem. Soc. 1990, 112, 6439. Ojima, I; Park, Y.H.; Sun, C.M.; Brigaud, T.; Zhao, M. Tetrahedron Lett. 1992, 33, 5737-5740. Okino, T.; Matsuda, H.; Murakami, J.Z.; Yamaguchi, K.Tetrahedron Lett. 1993, 34, 501. Jefford, C.W.; Wang, J.B.; Lu, Z.-H. Tetrahedron Lett. 1993, 34, 7557. Wagner, A.; Mollath, M. Tetrahedron Lett. 1993, 34, 619. Yang, L.; Weber, A.E.; Greenlee, W.J.; Patchett, A.A. Tetrahedron Lett. 1993, 34, 7035. Norman, B.H.; Morris, M.L. Tetrahedron Lett. 1992, 33, 6803. Dondoni, A.; Perrone, D. Synthesis, 1993, 1163. Compounds with anti configuration: Yuan, W.; Wong, C.-H.; Haeggström, J.Z.; Wetterholm, A.; Samuelsson, B. J. Am. Chem. Soc. 1992, 114, 6552. Bunnage, M.E.; Davies, S.G.; Goodwin, C.J. Synlett, 1993, 731-732.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 7557
    • Jefford, C.W.1    Wang, J.B.2    Lu, Z.-H.3
  • 9
    • 0027469088 scopus 로고
    • Compounds with syn configuration: Herranz, R.; Castro-Pichel, J.; García-López, T. Synthesis, 1989, 703. Pearson, W.H.; Hines, J.V.J. Org. Chem. 1989, 54, 4235-4237. Iizuka, K; Kamijo, T.; Harada, H.; Akahane, K.; Kubota, T.; Umeyama, H.; Kiso, Y.J. Chem. Soc. Chem. Commun. 1989, 1678- 1680. Matsumoto, T.; Kobayashi, Y.; Takemoto, Y.; Ito, Y.; Kamijo, T. Harada, H.; Terashima, S.Tetrahedron Lett. 1990, 29, 4175-4176. S. Hoover, D.J.; Damon, D.B. J. Am. Chem. Soc. 1990, 112, 6439. Ojima, I; Park, Y.H.; Sun, C.M.; Brigaud, T.; Zhao, M. Tetrahedron Lett. 1992, 33, 5737-5740. Okino, T.; Matsuda, H.; Murakami, J.Z.; Yamaguchi, K.Tetrahedron Lett. 1993, 34, 501. Jefford, C.W.; Wang, J.B.; Lu, Z.-H. Tetrahedron Lett. 1993, 34, 7557. Wagner, A.; Mollath, M. Tetrahedron Lett. 1993, 34, 619. Yang, L.; Weber, A.E.; Greenlee, W.J.; Patchett, A.A. Tetrahedron Lett. 1993, 34, 7035. Norman, B.H.; Morris, M.L. Tetrahedron Lett. 1992, 33, 6803. Dondoni, A.; Perrone, D. Synthesis, 1993, 1163. Compounds with anti configuration: Yuan, W.; Wong, C.-H.; Haeggström, J.Z.; Wetterholm, A.; Samuelsson, B. J. Am. Chem. Soc. 1992, 114, 6552. Bunnage, M.E.; Davies, S.G.; Goodwin, C.J. Synlett, 1993, 731-732.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 619
    • Wagner, A.1    Mollath, M.2
  • 10
    • 0027493648 scopus 로고
    • Compounds with syn configuration: Herranz, R.; Castro-Pichel, J.; García-López, T. Synthesis, 1989, 703. Pearson, W.H.; Hines, J.V.J. Org. Chem. 1989, 54, 4235-4237. Iizuka, K; Kamijo, T.; Harada, H.; Akahane, K.; Kubota, T.; Umeyama, H.; Kiso, Y.J. Chem. Soc. Chem. Commun. 1989, 1678- 1680. Matsumoto, T.; Kobayashi, Y.; Takemoto, Y.; Ito, Y.; Kamijo, T. Harada, H.; Terashima, S.Tetrahedron Lett. 1990, 29, 4175-4176. S. Hoover, D.J.; Damon, D.B. J. Am. Chem. Soc. 1990, 112, 6439. Ojima, I; Park, Y.H.; Sun, C.M.; Brigaud, T.; Zhao, M. Tetrahedron Lett. 1992, 33, 5737-5740. Okino, T.; Matsuda, H.; Murakami, J.Z.; Yamaguchi, K.Tetrahedron Lett. 1993, 34, 501. Jefford, C.W.; Wang, J.B.; Lu, Z.-H. Tetrahedron Lett. 1993, 34, 7557. Wagner, A.; Mollath, M. Tetrahedron Lett. 1993, 34, 619. Yang, L.; Weber, A.E.; Greenlee, W.J.; Patchett, A.A. Tetrahedron Lett. 1993, 34, 7035. Norman, B.H.; Morris, M.L. Tetrahedron Lett. 1992, 33, 6803. Dondoni, A.; Perrone, D. Synthesis, 1993, 1163. Compounds with anti configuration: Yuan, W.; Wong, C.-H.; Haeggström, J.Z.; Wetterholm, A.; Samuelsson, B. J. Am. Chem. Soc. 1992, 114, 6552. Bunnage, M.E.; Davies, S.G.; Goodwin, C.J. Synlett, 1993, 731-732.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 7035
    • Yang, L.1    Weber, A.E.2    Greenlee, W.J.3    Patchett, A.A.4
  • 11
    • 0026471808 scopus 로고
    • Compounds with syn configuration: Herranz, R.; Castro-Pichel, J.; García-López, T. Synthesis, 1989, 703. Pearson, W.H.; Hines, J.V.J. Org. Chem. 1989, 54, 4235-4237. Iizuka, K; Kamijo, T.; Harada, H.; Akahane, K.; Kubota, T.; Umeyama, H.; Kiso, Y.J. Chem. Soc. Chem. Commun. 1989, 1678- 1680. Matsumoto, T.; Kobayashi, Y.; Takemoto, Y.; Ito, Y.; Kamijo, T. Harada, H.; Terashima, S.Tetrahedron Lett. 1990, 29, 4175-4176. S. Hoover, D.J.; Damon, D.B. J. Am. Chem. Soc. 1990, 112, 6439. Ojima, I; Park, Y.H.; Sun, C.M.; Brigaud, T.; Zhao, M. Tetrahedron Lett. 1992, 33, 5737-5740. Okino, T.; Matsuda, H.; Murakami, J.Z.; Yamaguchi, K.Tetrahedron Lett. 1993, 34, 501. Jefford, C.W.; Wang, J.B.; Lu, Z.-H. Tetrahedron Lett. 1993, 34, 7557. Wagner, A.; Mollath, M. Tetrahedron Lett. 1993, 34, 619. Yang, L.; Weber, A.E.; Greenlee, W.J.; Patchett, A.A. Tetrahedron Lett. 1993, 34, 7035. Norman, B.H.; Morris, M.L. Tetrahedron Lett. 1992, 33, 6803. Dondoni, A.; Perrone, D. Synthesis, 1993, 1163. Compounds with anti configuration: Yuan, W.; Wong, C.-H.; Haeggström, J.Z.; Wetterholm, A.; Samuelsson, B. J. Am. Chem. Soc. 1992, 114, 6552. Bunnage, M.E.; Davies, S.G.; Goodwin, C.J. Synlett, 1993, 731-732.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 6803
    • Norman, B.H.1    Morris, M.L.2
  • 12
    • 0242715992 scopus 로고
    • Compounds with syn configuration: Herranz, R.; Castro-Pichel, J.; García-López, T. Synthesis, 1989, 703. Pearson, W.H.; Hines, J.V.J. Org. Chem. 1989, 54, 4235-4237. Iizuka, K; Kamijo, T.; Harada, H.; Akahane, K.; Kubota, T.; Umeyama, H.; Kiso, Y.J. Chem. Soc. Chem. Commun. 1989, 1678- 1680. Matsumoto, T.; Kobayashi, Y.; Takemoto, Y.; Ito, Y.; Kamijo, T. Harada, H.; Terashima, S.Tetrahedron Lett. 1990, 29, 4175-4176. S. Hoover, D.J.; Damon, D.B. J. Am. Chem. Soc. 1990, 112, 6439. Ojima, I; Park, Y.H.; Sun, C.M.; Brigaud, T.; Zhao, M. Tetrahedron Lett. 1992, 33, 5737-5740. Okino, T.; Matsuda, H.; Murakami, J.Z.; Yamaguchi, K.Tetrahedron Lett. 1993, 34, 501. Jefford, C.W.; Wang, J.B.; Lu, Z.-H. Tetrahedron Lett. 1993, 34, 7557. Wagner, A.; Mollath, M. Tetrahedron Lett. 1993, 34, 619. Yang, L.; Weber, A.E.; Greenlee, W.J.; Patchett, A.A. Tetrahedron Lett. 1993, 34, 7035. Norman, B.H.; Morris, M.L. Tetrahedron Lett. 1992, 33, 6803. Dondoni, A.; Perrone, D. Synthesis, 1993, 1163. Compounds with anti configuration: Yuan, W.; Wong, C.-H.; Haeggström, J.Z.; Wetterholm, A.; Samuelsson, B. J. Am. Chem. Soc. 1992, 114, 6552. Bunnage, M.E.; Davies, S.G.; Goodwin, C.J. Synlett, 1993, 731-732.
    • (1993) Synthesis , pp. 1163
    • Dondoni, A.1    Perrone, D.2
  • 13
    • 0010392869 scopus 로고
    • Compounds with syn configuration: Herranz, R.; Castro-Pichel, J.; García-López, T. Synthesis, 1989, 703. Pearson, W.H.; Hines, J.V.J. Org. Chem. 1989, 54, 4235-4237. Iizuka, K; Kamijo, T.; Harada, H.; Akahane, K.; Kubota, T.; Umeyama, H.; Kiso, Y.J. Chem. Soc. Chem. Commun. 1989, 1678- 1680. Matsumoto, T.; Kobayashi, Y.; Takemoto, Y.; Ito, Y.; Kamijo, T. Harada, H.; Terashima, S.Tetrahedron Lett. 1990, 29, 4175-4176. S. Hoover, D.J.; Damon, D.B. J. Am. Chem. Soc. 1990, 112, 6439. Ojima, I; Park, Y.H.; Sun, C.M.; Brigaud, T.; Zhao, M. Tetrahedron Lett. 1992, 33, 5737-5740. Okino, T.; Matsuda, H.; Murakami, J.Z.; Yamaguchi, K.Tetrahedron Lett. 1993, 34, 501. Jefford, C.W.; Wang, J.B.; Lu, Z.-H. Tetrahedron Lett. 1993, 34, 7557. Wagner, A.; Mollath, M. Tetrahedron Lett. 1993, 34, 619. Yang, L.; Weber, A.E.; Greenlee, W.J.; Patchett, A.A. Tetrahedron Lett. 1993, 34, 7035. Norman, B.H.; Morris, M.L. Tetrahedron Lett. 1992, 33, 6803. Dondoni, A.; Perrone, D. Synthesis, 1993, 1163. Compounds with anti configuration: Yuan, W.; Wong, C.-H.; Haeggström, J.Z.; Wetterholm, A.; Samuelsson, B. J. Am. Chem. Soc. 1992, 114, 6552. Bunnage, M.E.; Davies, S.G.; Goodwin, C.J. Synlett, 1993, 731-732.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 6552
    • Yuan, W.1    Wong, C.-H.2    Haeggström, J.Z.3    Wetterholm, A.4    Samuelsson, B.5
  • 14
    • 84988114394 scopus 로고
    • Compounds with syn configuration: Herranz, R.; Castro-Pichel, J.; García-López, T. Synthesis, 1989, 703. Pearson, W.H.; Hines, J.V.J. Org. Chem. 1989, 54, 4235-4237. Iizuka, K; Kamijo, T.; Harada, H.; Akahane, K.; Kubota, T.; Umeyama, H.; Kiso, Y.J. Chem. Soc. Chem. Commun. 1989, 1678- 1680. Matsumoto, T.; Kobayashi, Y.; Takemoto, Y.; Ito, Y.; Kamijo, T. Harada, H.; Terashima, S.Tetrahedron Lett. 1990, 29, 4175-4176. S. Hoover, D.J.; Damon, D.B. J. Am. Chem. Soc. 1990, 112, 6439. Ojima, I; Park, Y.H.; Sun, C.M.; Brigaud, T.; Zhao, M. Tetrahedron Lett. 1992, 33, 5737-5740. Okino, T.; Matsuda, H.; Murakami, J.Z.; Yamaguchi, K.Tetrahedron Lett. 1993, 34, 501. Jefford, C.W.; Wang, J.B.; Lu, Z.-H. Tetrahedron Lett. 1993, 34, 7557. Wagner, A.; Mollath, M. Tetrahedron Lett. 1993, 34, 619. Yang, L.; Weber, A.E.; Greenlee, W.J.; Patchett, A.A. Tetrahedron Lett. 1993, 34, 7035. Norman, B.H.; Morris, M.L. Tetrahedron Lett. 1992, 33, 6803. Dondoni, A.; Perrone, D. Synthesis, 1993, 1163. Compounds with anti configuration: Yuan, W.; Wong, C.-H.; Haeggström, J.Z.; Wetterholm, A.; Samuelsson, B. J. Am. Chem. Soc. 1992, 114, 6552. Bunnage, M.E.; Davies, S.G.; Goodwin, C.J. Synlett, 1993, 731-732.
    • (1993) Synlett , pp. 731-732
    • Bunnage, M.E.1    Davies, S.G.2    Goodwin, C.J.3
  • 17
    • 0028057842 scopus 로고
    • Some representative enantioselective synthesis of the Taxol and/or Taxotere® side chain: (a) Denis, J.N.; Kanazawa, A.M.; Greene, A.E. Tetrahedron Lett. 1994, 35, 105. Kanazawa, A.M.; Greene, A.E. J. Org. Chem. 1994, 59, 1238. Kanazawa, A.M.; Greene, A.E. J. Chem. Soc. Chem. Commun. 1994, 2591. Kanazawa, A.M.; Denis, J.N.; Correa, A.; Greene, A.E. J. Org. Chem. 1993, 58, 255.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 105
    • Denis, J.N.1    Kanazawa, A.M.2    Greene, A.E.3
  • 18
    • 0028346095 scopus 로고
    • Some representative enantioselective synthesis of the Taxol and/or Taxotere® side chain: (a) Denis, J.N.; Kanazawa, A.M.; Greene, A.E. Tetrahedron Lett. 1994, 35, 105. Kanazawa, A.M.; Greene, A.E. J. Org. Chem. 1994, 59, 1238. Kanazawa, A.M.; Greene, A.E. J. Chem. Soc. Chem. Commun. 1994, 2591. Kanazawa, A.M.; Denis, J.N.; Correa, A.; Greene, A.E. J. Org. Chem. 1993, 58, 255.
    • (1994) J. Org. Chem. , vol.59 , pp. 1238
    • Kanazawa, A.M.1    Greene, A.E.2
  • 19
    • 0027970579 scopus 로고
    • Some representative enantioselective synthesis of the Taxol and/or Taxotere® side chain: (a) Denis, J.N.; Kanazawa, A.M.; Greene, A.E. Tetrahedron Lett. 1994, 35, 105. Kanazawa, A.M.; Greene, A.E. J. Org. Chem. 1994, 59, 1238. Kanazawa, A.M.; Greene, A.E. J. Chem. Soc. Chem. Commun. 1994, 2591. Kanazawa, A.M.; Denis, J.N.; Correa, A.; Greene, A.E. J. Org. Chem. 1993, 58, 255.
    • (1994) J. Chem. Soc. Chem. Commun. , pp. 2591
    • Kanazawa, A.M.1    Greene, A.E.2
  • 20
    • 0027465868 scopus 로고
    • Some representative enantioselective synthesis of the Taxol and/or Taxotere® side chain: (a) Denis, J.N.; Kanazawa, A.M.; Greene, A.E. Tetrahedron Lett. 1994, 35, 105. Kanazawa, A.M.; Greene, A.E. J. Org. Chem. 1994, 59, 1238. Kanazawa, A.M.; Greene, A.E. J. Chem. Soc. Chem. Commun. 1994, 2591. Kanazawa, A.M.; Denis, J.N.; Correa, A.; Greene, A.E. J. Org. Chem. 1993, 58, 255.
    • (1993) J. Org. Chem. , vol.58 , pp. 255
    • Kanazawa, A.M.1    Denis, J.N.2    Correa, A.3    Greene, A.E.4
  • 24
    • 0027380234 scopus 로고
    • (d) Commerçon, A.; Bézard, D.; Bernard, F.; Bourzart, J.D. Tetrahedron Lett. 1992, 33, 5185. Commerçon, A.; Bourzart, J.D. Tetrahedron Lett. 1993, 34, 6049.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 6049
    • Commerçon, A.1    Bourzart, J.D.2
  • 43
    • 0025050730 scopus 로고
    • In most protease inhibitors the relative configuration of the oc-hydroxy-β-amino acid fragment is syn. lizuka, K; Kamijo, T.; Harada, H.; Akahane, K.; Kubota, T.; Umeyama, H.; Ishida, T.; Kiso, Y. J. Med. Chem. 1990, 33, 2707-2714. Nishizawa, R.; Saino, T.; Takita, T.; Suda, H; Aoyagi, T.; Umezawa, H. J. Med. Chem. 1977, 20, 510.
    • (1990) J. Med. Chem. , vol.33 , pp. 2707-2714
    • Lizuka, K.1    Kamijo, T.2    Harada, H.3    Akahane, K.4    Kubota, T.5    Umeyama, H.6    Ishida, T.7    Kiso, Y.8
  • 44
    • 0017596420 scopus 로고
    • In most protease inhibitors the relative configuration of the oc-hydroxy-β-amino acid fragment is syn. lizuka, K; Kamijo, T.; Harada, H.; Akahane, K.; Kubota, T.; Umeyama, H.; Ishida, T.; Kiso, Y. J. Med. Chem. 1990, 33, 2707-2714. Nishizawa, R.; Saino, T.; Takita, T.; Suda, H; Aoyagi, T.; Umezawa, H. J. Med. Chem. 1977, 20, 510.
    • (1977) J. Med. Chem. , vol.20 , pp. 510
    • Nishizawa, R.1    Saino, T.2    Takita, T.3    Suda, H.4    Aoyagi, T.5    Umezawa, H.6
  • 45
    • 85030189436 scopus 로고    scopus 로고
    • note
    • For an attempted related strategy involving simultaneous N/O protection and its evolution into an O/O simultaneous protection strategy see ref.4
  • 48
    • 85030190805 scopus 로고    scopus 로고
    • unpublished results
    • Our best results in the epoxidation of (Z)-cinnamyl alcohol are, after 4 days of reaction at -30°C, 65% yield and 76% ee. The best reaction yield in the nucleophilic opening is 9%. Pastó, M.; Moyano, A.; Pericàs, M.A.; Riera, A., unpublished results.
    • Pastó, M.1    Moyano, A.2    Pericàs, M.A.3    Riera, A.4
  • 62
    • 85030186633 scopus 로고    scopus 로고
    • note
    • Even very careful acidic treatments at the work-up stage afford mixtures of α-hydroxy acid 19 and its 1-ethoxy ethoxy acetal.


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