Literature DB >> 18489157

Evolution of natural product scaffolds by acyl- and arylnitroso hetero-diels-alder reactions: new chemistry on piperine.

Viktor Krchnák1, Katherine R Waring, Bruce C Noll, Ute Moellmann, Hans-Martin Dahse, Marvin J Miller.   

Abstract

Piperine, a natural product containing a conjugated diene, was reacted with polymer-supported acyl- and arylnitroso dienophiles. The reactions with arylnitroso dienophiles were also carried out in solution. The oxazine rings formed by the corresponding hetero-Diels-Alder reactions were further transformed and novel acyclic as well as heterocyclic derivatives including pyrroles and quinoxalinones were prepared.

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Year:  2008        PMID： 18489157     DOI： 10.1021/jo8004827

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  14 in total

1.  Selective molecular sequestration with concurrent natural product functionalization and derivatization: from crude natural product extracts to a single natural product derivative in one step.

Authors:  Viktor Krchňák; Jaroslav Zajíček; Patricia A Miller; Marvin J Miller
Journal:  J Org Chem       Date:  2011-11-16       Impact factor: 4.354

Review 2.  Nitroso Diels-Alder (NDA) reaction as an efficient tool for the functionalization of diene-containing natural products.

Authors:  Serena Carosso; Marvin J Miller
Journal:  Org Biomol Chem       Date:  2014-10-14       Impact factor: 3.876

3.  N-O chemistry for antibiotics: discovery of N-alkyl-N-(pyridin-2-yl)hydroxylamine scaffolds as selective antibacterial agents using nitroso Diels-Alder and ene chemistry.

Authors:  Timothy A Wencewicz; Baiyuan Yang; James R Rudloff; Allen G Oliver; Marvin J Miller
Journal:  J Med Chem       Date:  2011-09-15       Impact factor: 7.446

Review 4.  The nitrosocarbonyl hetero-Diels-Alder reaction as a useful tool for organic syntheses.

Authors:  Brian S Bodnar; Marvin J Miller
Journal:  Angew Chem Int Ed Engl       Date:  2011-04-21       Impact factor: 15.336

5.  Syntheses of new spirocarbocyclic nucleoside analogs using iminonitroso Diels-Alder reactions.

Authors:  Weimin Lin; Anuradha Gupta; Kyung Hee Kim; David Mendel; Marvin J Miller
Journal:  Org Lett       Date:  2009-01-15       Impact factor: 6.005

Review 6.  Chemo- and site-selective derivatizations of natural products enabling biological studies.

Authors:  Omar Robles; Daniel Romo
Journal:  Nat Prod Rep       Date:  2014-03       Impact factor: 13.423

7.  Preparation and biological evaluation of novel leucomycin analogs derived from nitroso Diels-Alder reactions.

Authors:  Baiyuan Yang; Tina Zöllner; Peter Gebhardt; Ute Möllmann; Marvin J Miller
Journal:  Org Biomol Chem       Date:  2009-12-11       Impact factor: 3.876

8.  Regio- and stereoselective indium triflate-mediated nucleophilic ring-opening reactions of 3-aza-2-oxabicyclo[2.2.1]hept-5-ene and -[2.2.2]oct-5-ene systems.

Authors:  Baiyuan Yang; Marvin J Miller
Journal:  J Org Chem       Date:  2009-10-16       Impact factor: 4.354

9.  Syntheses and biological studies of novel spiropiperazinyl oxazolidinone antibacterial agents using a spirocyclic diene derived acylnitroso Diels-Alder reaction.

Authors:  Cheng Ji; Weimin Lin; Garrett C Moraski; Jane A Thanassi; Michael J Pucci; Scott G Franzblau; Ute Möllmann; Marvin J Miller
Journal:  Bioorg Med Chem       Date:  2012-04-18       Impact factor: 3.641

10.  Syntheses and biological activity studies of novel sterol analogs from nitroso Diels-Alder reactions of ergosterol.

Authors:  Baiyuan Yang; Patricia A Miller; Ute Möllmann; Marvin J Miller
Journal:  Org Lett       Date:  2009-07-02       Impact factor: 6.005
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