Literature DB >> 23157463

Photoassisted access to enantiopure conformationally locked ribofuranosylamines spiro-linked to oxazolidino-diketopiperazines.

Nitin S Nandurkar1, N N Bhuvan Kumar, Olga A Mukhina, Andrei G Kutateladze.   

Abstract

N-Furoylated L-threonine-, serine-, or cysteine-based aminoacetals are coupled with o-aminoketones or aldehydes to offer rapid access to diverse enantiopure polyheterocycles possessing conformationally locked aminoglycoside-containing molecular scaffolds. The key step involves photogeneration of azaxylylenes which undergo [4 + 4] or [4 + 2] cycloadditions to the tethered furoyl pendants.

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Year:  2012        PMID： 23157463      PMCID： PMC3625677          DOI： 10.1021/co3001296

Source DB:  PubMed          Journal:  ACS Comb Sci        ISSN： 2156-8944            Impact factor:   3.784


  10 in total

1.  Lessons in molecular recognition: the effects of ligand and protein flexibility on molecular docking accuracy.

Authors:  Jon A Erickson; Mehran Jalaie; Daniel H Robertson; Richard A Lewis; Michal Vieth
Journal:  J Med Chem       Date:  2004-01-01       Impact factor: 7.446

Review 2.  The combinatorial synthesis of bicyclic privileged structures or privileged substructures.

Authors:  Douglas A Horton; Gregory T Bourne; Mark L Smythe
Journal:  Chem Rev       Date:  2003-03       Impact factor: 60.622

3.  Probing excited-state dynamics and intramolecular proton transfer in 1-acylaminoanthraquinones via the intermolecular solvent response.

Authors:  Sarah J Schmidtke; David F Underwood; David A Blank
Journal:  J Phys Chem A       Date:  2005-08-18       Impact factor: 2.781

4.  Rapid photoassisted access to N,O,S-polyheterocycles with benzoazocine and hydroquinoline cores: intramolecular cycloadditions of photogenerated azaxylylenes.

Authors:  Olga A Mukhina; N N Bhuvan Kumar; Teresa M Arisco; Roman A Valiulin; Greg A Metzel; Andrei G Kutateladze
Journal:  Angew Chem Int Ed Engl       Date:  2011-08-31       Impact factor: 15.336

5.  Quantum-chemical simulation of 1H NMR spectra. 2. Comparison of DFT-based procedures for computing proton-proton coupling constants in organic molecules.

Authors:  Thomas Bally; Paul R Rablen
Journal:  J Org Chem       Date:  2011-05-16       Impact factor: 4.354

6.  Molecular properties that influence the oral bioavailability of drug candidates.

Authors:  Daniel F Veber; Stephen R Johnson; Hung-Yuan Cheng; Brian R Smith; Keith W Ward; Kenneth D Kopple
Journal:  J Med Chem       Date:  2002-06-06       Impact factor: 7.446

7.  Double-tandem [4π+2π]·[2π+2π]·[4π+2π]·[2π+2π] synthetic sequence with photoprotolytic oxametathesis and photoepoxidation in the chromone series.

Authors:  Roman A Valiulin; Teresa M Arisco; Andrei G Kutateladze
Journal:  J Org Chem       Date:  2011-01-26       Impact factor: 4.354

8.  First Example of Intramolecular [2pi+2pi] Alkene-Arene Photocyclization in the Chromone Series and its Synthetic Utility.

Authors:  Roman A Valiulin; Andrei G Kutateladze
Journal:  Tetrahedron Lett       Date:  2010-07-21       Impact factor: 2.415

9.  Strained to the limit: when a cyclobutyl moiety becomes a thermodynamic sink in a protolytic ring-opening of photogenerated oxetanes.

Authors:  Roman A Valiulin; Teresa M Arisco; Andrei G Kutateladze
Journal:  Org Lett       Date:  2010-08-06       Impact factor: 6.005

10.  Harvesting the strain installed by a Paternò-Büchi step in a synthetically useful way: high-yielding photoprotolytic oxametathesis in polycyclic systems.

Authors:  Roman A Valiulin; Andrei G Kutateladze
Journal:  Org Lett       Date:  2009-09-03       Impact factor: 6.005
  10 in total
  8 in total

1.  Oxazolines as Dual-Function Traceless Chromophores and Chiral Auxiliaries: Enantioselective Photoassisted Synthesis of Polyheterocyclic Ketones.

Authors:  Olga A Mukhina; Andrei G Kutateladze
Journal:  J Am Chem Soc       Date:  2016-02-16       Impact factor: 15.419

2.  Amino Azaxylylenes Photogenerated from o-Amido Imines: Photoassisted Access to Complex Spiro-Poly-Heterocycles.

Authors:  Olga A Mukhina; Dmitry M Kuznetsov; Teresa M Cowger; Andrei G Kutateladze
Journal:  Angew Chem Int Ed Engl       Date:  2015-06-30       Impact factor: 15.336

3.  Conformationally Constrained Penta(hetero)cyclic Molecular Architectures via Photoassisted Diversity-Oriented Synthesis.

Authors:  Weston J Umstead; Olga A Mukhina; Dr Andrei G Kutateladze
Journal:  European J Org Chem       Date:  2015-04-01

4.  Photoassisted Synthesis of Complex Molecular Architectures: Dearomatization of Benzenoid Arenes with Aza-o-xylylenes via an Unprecedented [2+4] Reaction Topology.

Authors:  Dmitry M Kuznetsov; Olga A Mukhina; Andrei G Kutateladze
Journal:  Angew Chem Int Ed Engl       Date:  2016-04-21       Impact factor: 15.336

5.  Photoassisted access to complex polyheterocycles containing a β-lactam moiety.

Authors:  Weston J Umstead; Olga A Mukhina; Andrei G Kutateladze
Journal:  J Photochem Photobiol A Chem       Date:  2016-07-07       Impact factor: 4.291

6.  Photoinduced Cycloadditions in the Diversity-Oriented Synthesis Toolbox: Increasing Complexity with Straightforward Postphotochemical Modifications.

Authors:  Weston J Umstead; Olga A Mukhina; N N Bhuvan Kumar; Andrei G Kutateladze
Journal:  Aust J Chem       Date:  2015-07-24       Impact factor: 1.321

7.  Photoassisted synthesis of enantiopure alkaloid mimics possessing unprecedented polyheterocyclic cores.

Authors:  N N Bhuvan Kumar; Olga A Mukhina; Andrei G Kutateladze
Journal:  J Am Chem Soc       Date:  2013-06-21       Impact factor: 15.419

8.  Photoassisted diversity-oriented synthesis: accessing 2,6-epoxyazocane (oxamorphan) cores.

Authors:  Olga A Mukhina; N N Bhuvan Kumar; Teresa M Cowger; Andrei G Kutateladze
Journal:  J Org Chem       Date:  2014-11-05       Impact factor: 4.354
  8 in total

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