Transformation of Carbohydrate Derived 4-Azidopentanals Into Highly Functionalized Pyrrolidines Via a Tandem Staudinger/aza-Wittig/Ugi Multicomponent Reaction

The preparation of highly functionalized pyrrolidines by a tandem Staudinger/aza-Wittig/ Ugi Three-Component Reaction (SAWU-3CR) is presented. The SAWU-3CR was applied on two different carbohydrate derived 4-azidopentanals and two libraries of chemically diverse products were prepared.

[1]  Stefan Bräse,et al.  Organic azides: an exploding diversity of a unique class of compounds. , 2005, Angewandte Chemie.

[2]  M. Yus,et al.  Asymmetric multicomponent reactions (AMCRs): the new frontier. , 2005, Angewandte Chemie.

[3]  Carol M. Taylor,et al.  The impact of pyrrolidine hydroxylation on the conformation of proline-containing peptides. , 2005, The Journal of organic chemistry.

[4]  Benjamin G Davis,et al.  Glyco- and peptidomimetics from three-component Joullié-Ugi coupling show selective antiviral activity. , 2005, Journal of the American Chemical Society.

[5]  Jieping Zhu,et al.  Multicomponent Reactions: ZHU:MULTICOMPONENT REACTIONS O-BK , 2005 .

[6]  Mattie S. M. Timmer,et al.  Synthesis of functionalized heterocycles via a tandem Staudinger/aza-Wittig/Ugi multicomponent reaction , 2005 .

[7]  A. Basso,et al.  Enantio- and diastereoselective synthesis of 2,5-disubstituted pyrrolidines through a multicomponent Ugi reaction and their transformation into bicyclic scaffolds , 2004 .

[8]  P. Vogel,et al.  Synthesis of d- and l-2,3-trans-3,4-cis-4,5-trans-3,4-dihydroxy-5-hydroxymethylproline and tripeptides containing them. , 2004, The Journal of organic chemistry.

[9]  B. G. Davis,et al.  Highly diastereoselective additions to polyhydroxylated pyrrolidine cyclic imines: ready elaboration of aza-sugar scaffolds to create diverse carbohydrate-processing enzyme probes. , 2003, Chemistry.

[10]  M. Greef,et al.  Recent Advances in Solution-Phase Multicomponent Methodology for the Synthesis of Heterocyclic Compounds , 2003 .

[11]  Jieping Zhu.  Recent Developments in the Isonitrile‐Based Multicomponent Synthesis of Heterocycles , 2003 .

[12]  A. Dömling.  Recent advances in isocyanide-based multicomponent chemistry. , 2002, Current opinion in chemical biology.

[13]  T. Chakraborty,et al.  Studies on novel peptidomimetics having bi-directional dispositions of hydroxylated D-Pro-Gly motifs anchored on a C(2)-symmetric iminosugar-based foundation. , 2002, The Journal of organic chemistry.

[14]  S. Withers,et al.  Novel, lipophilic derivatives of 2,5-dideoxy-2,5-imino-D-mannitol (DMDP) are powerful beta-glucosidase inhibitors. , 2001, Bioorganic & medicinal chemistry letters.

[15]  I. Ugi,et al.  The multicomponent reactions and their libraries for natural and preparative chemistry. , 2001, Combinatorial chemistry & high throughput screening.

[16]  I. Ugi,et al.  Multicomponent Reactions with Isocyanides. , 2000, Angewandte Chemie.

[17]  R. Molyneux,et al.  Sugar-mimic glycosidase inhibitors: natural occurrence, biological activity and prospects for therapeutic application , 2000 .

[18]  I. Ugi,et al.  Multicomponent reactions. II. Stereoselective synthesis of 1(S)‐camphor‐2‐cis‐methylidene‐isocyanide and its application in Passerini‐ and Ugi‐reaction , 1997 .

[19]  R. Madsen,et al.  The Pent-4-enoyl Group: A Novel Amine-Protecting Group That Is Readily Cleaved under Mild Conditions , 1995 .

[20]  S. Ohta,et al.  Total syntheses of de-branched nagstatin and its analogs having glycosidase inhibiting activities , 1995 .

[21]  M. Joullié,et al.  Observations on the Stereochemical Outcome of the UGI Four-Component Condensation , 1989 .

[22]  P. Carroll,et al.  Model studies directed toward the total synthesis of 14-membered cyclopeptide alkaloids: synthesis of prolyl peptides via a four-component condensation , 1989 .

[23]  F. G. de las Heras,et al.  Synthesis of N-(2-acetamido-2,3-dideoxy-D-glucopyranos-3-yl)glycyl-L-alanyl-D -isoglutamine analogues of muramyl dipeptide. , 1986, Carbohydrate research.

[24]  A. J. Papa.  Synthesis and Azidolysis of 2-Chlorotetramethylguanidine. Synthetic Utility of Hexa- and Tetramethylguanidinium Azide , 1966 .