Literature DB >> 17602642

Iminonitroso Diels-Alder reactions for efficient derivatization and functionalization of complex diene-containing natural products.

Fangzheng Li1, Baiyuan Yang, Marvin J Miller, Jaroslav Zajicek, Bruce C Noll, Ute Möllmann, Hans-Martin Dahse, Patricia A Miller.   

Abstract

A remarkably efficient method for derivatization of complex diene-containing natural products by using stabilized iminonitroso Diels-Alder reactions is described. Turimycin H3, ergosterol, reductiomycin, isoforocidin, colchicine and thebaine were found to react with nitrosopyridines in a highly efficient regio- and stereoselective fashion. Preliminary bioactivity evaluations of turimycin cycloadducts are reported.

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Year:  2007        PMID： 17602642     DOI： 10.1021/ol071322b

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  18 in total

1.  A new sensitive LC/MS/MS analysis of vitamin D metabolites using a click derivatization reagent, 2-nitrosopyridine.

Authors:  Debin Wan; Jun Yang; Bogdan Barnych; Sung Hee Hwang; Kin Sing Stephen Lee; Yongliang Cui; Jun Niu; Mitchell A Watsky; Bruce D Hammock
Journal:  J Lipid Res       Date:  2017-02-01       Impact factor: 5.922

2.  Syntheses and biological evaluation of ring-C modified colchicine analogs.

Authors:  Baiyuan Yang; Zhiqing C Zhu; Holly V Goodson; Marvin J Miller
Journal:  Bioorg Med Chem Lett       Date:  2010-03-15       Impact factor: 2.823

3.  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

4.  Reactions of hexadehydro-Diels-Alder benzynes with structurally complex multifunctional natural products.

Authors:  Sean P Ross; Thomas R Hoye
Journal:  Nat Chem       Date:  2017-02-27       Impact factor: 24.427

Review 5.  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

6.  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

7.  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 8.  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

9.  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

10.  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
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