Studies on cyclization reactions of 3-amino-2,4-dihydroxybutanoic acid derivatives.

A number of cyclic derivatives of 3-amino-2,4-dihydroxybutanoic acid are known in the literature but they are often prepared from other cyclic precursors. This study showed that the title compound too may serve as a convenient substrate for cyclization reactions. Using orthogonally-protected linear derivatives, regioselective cyclizations were performed, leading to original and highly-functionalized γ-lactones, oxazolidinones, oxazolines and aziridines. In these reactions a key role was played by the C3 nitrogen group function, while the C2 alcohol function showed no propensity for participation in cyclization reactions.

[1]  Thao M. Nguyen,et al.  Synthetic Access to All Four Stereoisomers of Oxetin. , 2016, The Journal of organic chemistry.

[2]  Wenjing Chu,et al.  Design, synthesis, and structure-activity and structure-pharmacokinetic relationship studies of novel [6,6,5] tricyclic fused oxazolidinones leading to the discovery of a potent, selective, and orally bioavailable FXa inhibitor. , 2014, Journal of medicinal chemistry.

[3]  P. Finn,et al.  Substrate derived peptidic α-ketoamides as inhibitors of the malarial protease PfSUB1. , 2014, Bioorganic & medicinal chemistry letters.

[4]  P. Krishna,et al.  First Diastereoselective PasseriniSmiles and UgiSmiles Reactions Using Chiral Aldehydes , 2014 .

[5]  Sven Mangelinckx,et al.  Asymmetric synthesis of chloroisothreonine derivatives via syn-stereoselective Mannich-type additions across N-sulfinyl-α-chloroimines. , 2014, Organic & biomolecular chemistry.

[6]  Young Gyu Kim,et al.  N-Hydroxymethyl derivatives of α-amino aldehydes used for the stereoselective syntheses of β-amino-α-hydroxy acids , 2014 .

[7]  James A. Lee,et al.  Trading N and O: asymmetric syntheses of β-hydroxy-α-amino acids via α-hydroxy-β-amino esters , 2013 .

[8]  C. Santos,et al.  Rapid access to jaspine B and its enantiomer , 2013 .

[9]  Jae Nyoung Kim,et al.  An efficient synthesis of α-methylene-γ-butyrolactones from Baylis–Hillman adducts via an In-mediated Barbier reaction and stereoselective lactonization under MeSO2Cl/Et3N conditions , 2010 .

[10]  M. Shibuya,et al.  One-Pot Synthesis of α-SiloxyEsters Using a Silylated Masked Acyl Cyanide , 2008 .

[11]  J. Louie,et al.  Nickel-catalyzed reactions of vinyl aziridines and aziridinylen-ynes. , 2008, Tetrahedron letters.

[12]  D. Aitken,et al.  Total synthesis of cyclotheonamide C using a tandem backbone-extension-coupling methodology. , 2008, Angewandte Chemie.

[13]  S. Davies,et al.  Asymmetric synthesis of vicinal amino alcohols: xestoaminol C, sphinganine and sphingosine. , 2008, Organic & biomolecular chemistry.

[14]  J. E. Thomson,et al.  Asymmetric synthesis of N,O,O,O-tetra-acetyl d-lyxo-phytosphingosine, jaspine B (pachastrissamine) and its C(2)-epimer , 2007 .

[15]  C. Hutton,et al.  The enantioselective synthesis of APTO and AETD: polyhydroxylated beta-amino acid constituents of the microsclerodermin cyclic peptides. , 2007, Organic & biomolecular chemistry.

[16]  S. Davies,et al.  Asymmetric synthesis of 4-amino-γ-butyrolactones via lithium amide conjugate addition , 2007 .

[17]  Brian M. Frezza,et al.  A Simple γ-Backbone Modification Preorganizes Peptide Nucleic Acid into a Helical Structure , 2006 .

[18]  M. Skwarczynski,et al.  O-N intramolecular alkoxycarbonyl migration of typical protective groups in hydroxyamino acids. , 2006, The Journal of organic chemistry.

[19]  G. Simig,et al.  Regioselective reactions of mesyloxymethylazetidinones with nucleophiles I. Cleavage of the azetidinone ring, azetidinone-aziridine ring transformations , 2006 .

[20]  C. Pak,et al.  Facile conversion of 2-azetidinones to 2-piperidones: application to a formal synthesis of Prosopis and Cassia alkaloids , 2003 .

[21]  Xinming Li,et al.  A three-step preparation of MAC reagents from malononitrile , 2003 .

[22]  F. Couty,et al.  The Reactivity of the N-Boc Protecting Group: An Underrated Feature , 2002 .

[23]  Tsuyoshi Nakamura,et al.  Stereoselective synthesis of d-erythro-sphingosine and l-lyxo-phytosphingosine , 2001 .

[24]  S. Ko,et al.  Orthogonally protected, enantiopure syn-2-amino-1,3,4-butanetriol: a general building block for syn-amino alcohols. , 2001, The Journal of organic chemistry.

[25]  Ma,et al.  A new one-Pot method for the synthesis of alpha-siloxyamides from aldehydes or ketones and its application to the synthesis of (-)-bestatin , 2000, Organic letters.

[26]  Y. Shigeri,et al.  Syntheses of optically pure beta-hydroxyaspartate derivatives as glutamate transporter blockers. , 2000, Bioorganic & medicinal chemistry letters.

[27]  S. Franco,et al.  Nucleophilic Additions of 2-Furyllithium to Carbonyl Derivatives of L-Serine. Formal Synthesis of (2R,3R)-β-Hydroxy Aspartic Acid , 1998 .

[28]  J. Plattner,et al.  Synthesis and biological evaluation of C-3'-modified analogs of 9(R)-dihydrotaxol. , 1994, Journal of medicinal chemistry.

[29]  M. Pollastri,et al.  Loss of the tert-butyloxycarbonyl (Boc) protecting group under basic conditions , 1994 .

[30]  D. Dorsch,et al.  Stereoselective synthesis of (2S,3S)‐norstatine derivatives by addition of lithiated methoxyallene to amino aldehydes and subsequent ozonolysis , 1994 .

[31]  D. Perrone,et al.  2-Thiazolyl α-Amino Ketones: A New Class of Reactive Intermediates for the Stereocontrolled Synthesis of Unusual Amino Acids , 2010 .

[32]  S. Hanessian,et al.  Novel access to (3R)- and (3S)-3-hydroxy-L-aspartic acids, (4S)-4-hydroxy- L-glutamic acid, and related amino acids , 1993 .

[33]  F. Couty,et al.  Chiral oxazolidinones from N-Boc derivatives of β-amino alcohols. Effect of a N-methyl substituent on reactivity and stereoselectivity , 1993 .

[34]  M. Bols,et al.  ALPHA - OR BETA -AMINO POLYHYDROXY ACIDS FROM THE REACTION OF BROMODEOXYALDONOLACTONES WITH LIQUID AMMONIA , 1991 .

[35]  J. Tilley,et al.  Preparation of a protected (2S,3S)-.beta.-hydroxyaspartic acid suitable for solid-phase peptide synthesis , 1990 .

[36]  L. Prati,et al.  Diastereo- and Enantioselective Synthesis of Fluorinated Threonines , 1985 .

[37]  S. Ōmura,et al.  Oxetin, a new antimetabolite from an actinomycete. Fermentation, isolation, structure and biological activity. , 1984, The Journal of antibiotics.