Stereoselective elaboration of side chain residues in cyclopropane- containing dipeptide isosteres

Tetrahedron Letters

Volumn 40, Issue 15, 1999, Pages 2887-2890

  Martin, Stephen F ^a   Hom, Roy K ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIPEPTIDE DERIVATIVE; HYDRAZINE DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY; STEREOSPECIFICITY; STRUCTURE ANALYSIS;

EID: 0033537815     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00397-4     Document Type: Article

References (17)

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2. (b) Martin, S. F.; Dorsey, G. O.; Gane, T.; Hillier, M. C.; Kessler, H.; Baur, M.; Matha, B.; Erickson, J. W.; Bhat, T. N.; Munshi, S.; Gulnik, S. V.; Topol, I. A. J. Med. Chem. 1998, 41, 1581-1597.
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5. (c) Martin, S. F.; Dwyer, M. P. Tetrahedron Lett. 1998, 39, 1521-1524.
6. (d) Martin, S. F.; Hillier, M. C. Tetrahedron Lett. 1998, 39, 2929-2932.
7. 13C NMR, IR, and HRMS.
8. 1H NMR analysis of the crude reaction mixtures, and the minor isomer was typically not detected. Given the limitations of the NMR method, the dr is thus > 20:1.
9. 2O/pentane.
10. All reactions were run at 0.15-0.20 mmol scale and the reported yields have been duplicated.
11. For the preparation of the precursor alkyl iodide, see: Heslin, J. C.; Moody, C. J. J. Chem. Soc. Perkin Trans. 1 1988, 1417-1423.
12. (a) Claremon, D. A.; Lumma, P. K.; Philips, B. T. J. Am. Chem. Soc. 1986, 108, 8265-8266.
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