The stereocontrolled synthesis of orthogonally protected (R)-α- methyltryptophan

Tetrahedron Letters

Volumn 39, Issue 52, 1998, Pages 9589-9592

  Goodman, Murray ^a   Zhang, Jinfang ^a   Gantzel, Peter ^a   Benedetti, Ettore ^a,b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b Dipartimento di Chimica   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALANINE; N METHYLTRYPTOPHAN; TRYPTOPHAN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OPTICAL ROTATION; STEREOCHEMISTRY; X RAY DIFFRACTION;

EID: 0032564633     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02302-8     Document Type: Article

References (27)

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3. (c) Schiller, P. W. in Medicinal Chemistry for the 21st Century 1992, Ed. by Wermuth, C. G., Oxford Blackwell Scientific Publications, Chap 15, 215-232;
4. (d) Freidinger, R. M., ibid., Chap 16, 233-277,
5. (e) Jung, G., Beck-Sickinger, A. G.. Chem. Int. Ed. Engl. 1992, 31, 367-383.
6. (f) Hanessian, S., McNaughton-Smith, G., Lombart, H.-G., Lubell, W. D. Tetrahedron 1997, 53, 12789-12854.
7. 2. Reviews for the syntheses: (a) Coppola, G. M.; Shuster, H. F. Asymmetric Synthesis, Construction of Chiral Molecules Using Amino Acids, John Wiley & Sons, New York, 1987;
8. (b) Williams, R. W. Synthesis of Optically Active a-Amino Acids, Pergamon Press, London, 1989;
9. (c) O'Donnell, Martin J., Ed. α-Amino Acid Synthesis.Tetrahedron 1988, 44, 5253-5614..
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12. (c) Shao, H., Goodman, M., J. Org. Chem.. 1996, 61, 2582-2583;
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15. 4. A brief description of the overall reactions to obtain the materials is contained in our recent article. Goodman, M., Zhang, J. Chemtract 1997, 629-645;
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24. 2), 6.42 (s, 1H, CH), 6.91-7.90 (m, 9H, aromatic-H). MS (FAB+): m/z 449 (M+ H+).
25. 10. The bromide 4 was prepared from the corresponding alcohol by using a known procedure. Venkatachalam, T. K., Mzengeza, S, Diksic, M. Org. Prep. Proc. Int. 1993, 25, 249-251.
26. 11. The high enantiomeric purity of 6 was determined by the NMR studies of both diastereomeric Mosher esters from R-(-) and S-(+) Mosher's acid chloride.
27. 12. Strongly acidic conditions (6N HCl, reflux) were also examined, but only a trace amount of the free amino acid was obtained with the formation of another major by-product.