Asymmetric synthesis of building-blocks for peptides and peptidomimetics by means of the β-lactam synthon method

Recent advances in the syntheses of enantiopure synthetic building blocks useful for non-protein amino acids, dipeptides, oligopeptides using solid state peptide synthesis, isoserines (norstatines), dipeptide isosteres [hydroxy(keto)ethylene, hydroxyethylamine, hydroxyethylene and dihydroxyethylene isosteres], taxoids, polyamines, poly(amino alcohol)s and poly(amino ether)s, and other biologically active compounds through applications of the β-lactam Synthon method is reviewed.

[1]  J. Andersen.  Taxane Anticancer Agents: Basic Science and Current Status.Gunda I. Georg , Thomas T. Chen , Iwao Ojima , Dolatrai M. Vyas , 1997 .

[2]  S. Kuduk,et al.  Synthesis and Structure−Activity Relationships of Nonaromatic Taxoids: Effects of Alkyl and Alkenyl Ester Groups on Cytotoxicity , 1997 .

[3]  S. Kuduk,et al.  Syntheses and structure-activity relationships of taxoids derived from 14β-hydroxy-10-deacetylbaccatin III , 1997 .

[4]  J. Veith,et al.  Synthesis and biological activity of novel 3′-trifluoromethyl taxoids , 1997 .

[5]  P. Vrignaud,et al.  Syntheses and structure-activity relationships of the second-generation antitumor taxoids: exceptional activity against drug-resistant cancer cells. , 1996, Journal of medicinal chemistry.

[6]  Stella Huang,et al.  Diastereoselective addition of Grignard reagents to azetidine-2,3-dione: Synthesis of novel Taxol® analogues , 1996 .

[7]  M. Jayaraman,et al.  Application of (+)-(1S,2S)-2-amino-1-phenylpropan-1,3-diol in the formal total synthesis of carbapenems, novel 4-cyano-β-lactams and β-hydroxy aspartates , 1996 .

[8]  P. M. Deyà,et al.  Imine Substituent Effects on [2+2]Cycloadditions with Ketenes , 1996 .

[9]  S. Kuduk,et al.  Syntheses of new fluorine-containing taxoids by means of β-Lactam Synthon Method , 1996 .

[10]  K. Saigo,et al.  1(2,6-dichlorophenyl)ethylamine: a new and efficient chiral auxiliary for the Staudinger β-lactam synthesis , 1995 .

[11]  I. Ojima.  Recent Advances in the .beta.-Lactam Synthon Method , 1995 .

[12]  I. Ojima,et al.  Novel route to hydroxy(keto)ethylene dipeptide isosteres through the reaction of N-tBOC-β-lactams with enolates , 1995 .

[13]  S. Kapadia,et al.  Enantioselective synthesis of the (syn,anti)-1-amino-2,3-diol subunit of renin inhibitors by reaction of β-Lactams with a Grignard reagent , 1995 .

[14]  Michael L. Shuler,et al.  Taxol®: science and applications. , 1995 .

[15]  J. Odriozola,et al.  Concise General Synthesis of .alpha.,.gamma.-Disubstituted .beta.-Amino Ketones from .beta.-Lactams , 1994 .

[16]  G. Georg,et al.  An investigation of (R)-(+)-1-(1-naphthyl)ethylimines and (R)-(+)-1-(phenyl)ethylimines as chiral templates in the staudinger reaction , 1994 .

[17]  P. Colson,et al.  Asymmetric synthesis of .alpha.-alkyl-.alpha. amino acids from chromium-carbene-complex-derived .beta.-lactams , 1993 .

[18]  S. S. Bari,et al.  Stereoregulated synthesis of β-lactams from schiff bases derived from threonine esters , 1992 .

[19]  Yuko Kobayashi,et al.  A stereoselective synthesis of the (2R, 3S)- and (2S, 3R)-3-amino-2-hydroxybutyric acid derivatives, the key components of a renin inhibitor and bestatin. , 1992 .

[20]  M. Yamashita,et al.  Azetidines and bisazetidines. Their synthesis and use as the key intermediates to enantiomerically pure diamines, amino alcohols, and polyamines , 1991 .

[21]  J. Huff,et al.  HIV protease: a novel chemotherapeutic target for AIDS. , 1991, Journal of medicinal chemistry.

[22]  G. Teutsch,et al.  Enantioselective synthesis of a versatile 2-isocephem synthon , 1990 .

[23]  S. Thaisrivongs,et al.  Renin inhibitors. Design of angiotensinogen transition-state analogues containing novel. (2R,3R,4R,5S)-5-amino-3,4-dihydroxy-2-isopropyl-7-methyloctanoic acid. , 1987, Journal of medicinal chemistry.

[24]  I. Ojima,et al.  Remarkable effects of lone pair-lone pair interactions on the extremely stereoselective [2 + 2] cycloaddition of azidoketene to chiral 3-imino-.beta.-lactams , 1987 .

[25]  R. Cooper,et al.  Chiral control of the Staudinger reaction , 1987 .

[26]  Davidr . Evans,et al.  The asymmetric synthesis of β-lactam antibiotics - I. application of chiral oxazolidones in the staudinger reaction. , 1985 .

[27]  M. Jung.  Enzyme Inhibition by Amino Acids and their Derivatives , 1985 .