Application of the N-hydroxymethyl group to the stereoselective synthesis of (3S,4S)-3-aminodeoxystatine derivatives
作者： Dongwon Yoo , Seah Kwon , Young Gyu Kim
DOI: 10.1016/J.TETASY.2005.10.018
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摘要: Abstract Stereoselective synthesis of two 3-aminodeoxystatine derivatives was achieved. Chiral γ-amino-α,β-unsaturated esters containing an N -aminomethyl group undergo the stereoselective conjugate addition with internal carbamate or amide nitrogen nucleophile. The diastereoselectivity about 10:1 by 1 H NMR. Thus, were prepared from commercially available -Boc- l -leucine in nine steps overall yields 26% and 20% for benzyl acetamide derivatives, respectively.
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Matthew G. Bursavich, Daniel H. Rich, Designing non-peptide peptidomimetics in the 21st century: inhibitors targeting conformational ensembles. Journal of Medicinal Chemistry. ,vol. 45, pp. 541- 558 ,(2002) , 10.1021/JM010425B
Roy K. Hom, Larry Y. Fang, Shumeye Mamo, Jay S. Tung, Ashley C. Guinn, Don E. Walker, David L. Davis, Andrea F. Gailunas, Eugene D. Thorsett, Sukanto Sinha, Jeroen E. Knops, Nancy E. Jewett, John P. Anderson, Varghese John, Design and Synthesis of Statine-Based Cell-Permeable Peptidomimetic Inhibitors of Human β-Secretase Journal of Medicinal Chemistry. ,vol. 46, pp. 1799- 1802 ,(2003) , 10.1021/JM025619L
Daniel H. Rich, Eric T. O. Sun, Edgar Ulm, Synthesis of analogs of the carboxyl protease inhibitor pepstatin. Effect of structure on inhibition of pepsin and renin Journal of Medicinal Chemistry. ,vol. 23, pp. 27- 33 ,(1980) , 10.1021/JM00175A006
Dongwon Yoo, Joon Seok Oh, Young Gyu Kim, The N-hydroxymethyl group for stereoselective conjugate addition: application to the synthesis of (-)-statine. Organic Letters. ,vol. 4, pp. 1213- 1215 ,(2002) , 10.1021/OL025653U
Heinrich J. Schostarez, A stereospecific synthesis of 3-aminodeoxystatine Journal of Organic Chemistry. ,vol. 53, pp. 3628- 3631 ,(1988) , 10.1021/JO00250A046
Robert H. Bradbury, Janet E. Rivett, 1,2,4-Triazolo[4,3-a]pyrazine derivatives with human renin inhibitory activity. 3.1 Synthesis and biological properties of aminodeoxystatine and difluorostatone derivatives. Journal of Medicinal Chemistry. ,vol. 34, pp. 151- 157 ,(1991) , 10.1021/JM00105A022
Rolf A.T.M. van Benthem, Henk Hiemstra, Gema Rodríguez Longarela, W.Nico Speckamp, Formamide as a superior nitrogen nucleophile in palladium(II) mediated synthesis of imidazolidines Tetrahedron Letters. ,vol. 35, pp. 9281- 9284 ,(1994) , 10.1016/0040-4039(94)88488-9
Reinhard W. Hoffmann, Allylic 1,3-strain as a controlling factor in stereoselective transformations Chemical Reviews. ,vol. 89, pp. 1841- 1860 ,(1989) , 10.1021/CR00098A009
Seung Il Hyun, Young Gyu Kim, N-Hydroxymethyl group for configurationally stable N-alkoxycarbonyl α-amino aldehydes Tetrahedron Letters. ,vol. 39, pp. 4299- 4302 ,(1998) , 10.1016/S0040-4039(98)00715-1
Francis Johnson, Allylic strain in six-membered rings Chemical Reviews. ,vol. 68, pp. 375- 413 ,(1968) , 10.1021/CR60254A001