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Volumn 341, Issue 7, 1999, Pages 685-686

Stereocontrolled Synthesis of the Taxol C-13 Side Chain: Methyl (2R,3S)-3-Benzoylamino-2-hydroxy-3-phenylpropanoate

Author keywords

Allenes; Amino acids; Amino aldehydes; Lithiation; Ozonolysis

Indexed keywords


EID: 0347710606     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (11)

References (28)
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    • Review: K. C. Nicolaou, W.-M. Dai, R. K. Guy, Angew. Chem. 1994, 106, 38; Angew. Chem. Int. Ed. Engl. 1994, 33, 15 and references cited therein; Syntheses of the C-13 side chain since 1994: A. M. P. Koskinen, E. K. Karvinen, J. P. Siirilae, J. Chem. Soc., Chem. Commun. 1994, 21; D. G. I. Kingston, A. G. Chaudhary, A. A. L. Gunatilaka, M. L. Middleton, Tetrahedron Lett. 1994, 35, 4483; S. Hanessian, J.-Y. Sanceau, Can. J. Chem. 1996, 74, 621; G. Righi, G. Rumboldt, C. Bonini, J. Org. Chem. 1996, 61, 3557; Z. Hu, P. W. Erhardt, Org. Process Res. Dev. 1997, 1, 387; G. Cardillo, L. Gentilucci, A. Tolomelli, C. Tomasini, J. Org. Chem. 1998, 63, 2351; I. Shiina, K. Saitoh, I. Frechard-Ortuno, T. Mukaiyama, Chem. Lett. 1998, 3; D. Lee, M.-J. Kim, Tetrahedron Lett. 1998, 39, 2163; K.-Y. Lee, Y.-H. Kim, M.-S. Park, W.-H. Ham, Tetrahedron Lett. 1998, 39, 8129; P. Merino, E. Castillo, S. Franco, F. L. Merchán, T. Tejero, Tetrahedron 1998, 54, 12301
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    • Shiina, I.1    Saitoh, K.2    Frechard-Ortuno, I.3    Mukaiyama, T.4
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    • Review: K. C. Nicolaou, W.-M. Dai, R. K. Guy, Angew. Chem. 1994, 106, 38; Angew. Chem. Int. Ed. Engl. 1994, 33, 15 and references cited therein; Syntheses of the C-13 side chain since 1994: A. M. P. Koskinen, E. K. Karvinen, J. P. Siirilae, J. Chem. Soc., Chem. Commun. 1994, 21; D. G. I. Kingston, A. G. Chaudhary, A. A. L. Gunatilaka, M. L. Middleton, Tetrahedron Lett. 1994, 35, 4483; S. Hanessian, J.-Y. Sanceau, Can. J. Chem. 1996, 74, 621; G. Righi, G. Rumboldt, C. Bonini, J. Org. Chem. 1996, 61, 3557; Z. Hu, P. W. Erhardt, Org. Process Res. Dev. 1997, 1, 387; G. Cardillo, L. Gentilucci, A. Tolomelli, C. Tomasini, J. Org. Chem. 1998, 63, 2351; I. Shiina, K. Saitoh, I. Frechard-Ortuno, T. Mukaiyama, Chem. Lett. 1998, 3; D. Lee, M.-J. Kim, Tetrahedron Lett. 1998, 39, 2163; K.-Y. Lee, Y.-H. Kim, M.-S. Park, W.-H. Ham, Tetrahedron Lett. 1998, 39, 8129; P. Merino, E. Castillo, S. Franco, F. L. Merchán, T. Tejero, Tetrahedron 1998, 54, 12301
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    • The Dondoni procedure (ref. [4]) provided 3 with variable purity. A more reliable method could be the reduction/oxidation sequence according to Greene: A. Correa, J.-N. Denis, A. E. Greene, J. Org. Chem. 1991, 56, 6939
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