Literature DB >> 24161069

Tandem dienone photorearrangement-cycloaddition for the rapid generation of molecular complexity.

Pieter H Bos1, Mitchell T Antalek, John A Porco, Corey R J Stephenson.   

Abstract

A tandem dienone photorearrangement-cycloaddition (DPC) reaction of novel cyclohexadienone substrates tethered with various 2π and 4π reaction partners resulted in the formation of polycyclic, bridged frameworks. In particular, use of alkynyl ether-tethered substrates led to (3 + 2) cycloaddition to afford strained alkenes which could be further elaborated by intra- and intermolecular cycloaddition chemistry to produce complex, polycyclic chemotypes.

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Year:  2013        PMID: 24161069      PMCID: PMC3964885          DOI: 10.1021/ja409992m

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  24 in total

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Authors:  Shunyou Cai; Zheng Liu; Weibin Zhang; Xinyang Zhao; David Zhigang Wang
Journal:  Angew Chem Int Ed Engl       Date:  2011-09-29       Impact factor: 15.336

2.  Synthesis and reactivity of bicyclo[3.2.1]octanoid-derived cyclopropanes.

Authors:  John R Goodell; Jennifer L Poole; Aaron B Beeler; Jeffrey Aubé; John A Porco
Journal:  J Org Chem       Date:  2011-11-01       Impact factor: 4.354

3.  Photochemical reactions as key steps in organic synthesis.

Authors:  Norbert Hoffmann
Journal:  Chem Rev       Date:  2008-02-27       Impact factor: 60.622

4.  Micro-photochemistry: photochemistry in microstructured reactors. The new photochemistry of the future?

Authors:  Emma E Coyle; Michael Oelgemöller
Journal:  Photochem Photobiol Sci       Date:  2008-08-13       Impact factor: 3.982

5.  Parallel microflow photochemistry: process optimization, scale-up, and library synthesis.

Authors:  Alexander Yavorskyy; Oksana Shvydkiv; Norbert Hoffmann; Kieran Nolan; Michael Oelgemöller
Journal:  Org Lett       Date:  2012-08-20       Impact factor: 6.005

6.  Development of an automated microfluidic reaction platform for multidimensional screening: reaction discovery employing bicyclo[3.2.1]octanoid scaffolds.

Authors:  John R Goodell; Jonathan P McMullen; Nikolay Zaborenko; Jason R Maloney; Chuan-Xing Ho; Klavs F Jensen; John A Porco; Aaron B Beeler
Journal:  J Org Chem       Date:  2009-08-21       Impact factor: 4.354

7.  Continuous photochemical generation of catalytically active [CpRu]+ complexes from CpRu(η6-C6H6)PF6.

Authors:  Alicia C Gutierrez; Timothy F Jamison
Journal:  Org Lett       Date:  2011-11-15       Impact factor: 6.005

8.  Photosensitized addition of isopropanol to furanones in a 365 nm UV-LED microchip.

Authors:  Oksana Shvydkiv; Alexander Yavorskyy; Kieran Nolan; Ali Youssef; Emmanuel Riguet; Norbert Hoffmann; Michael Oelgemöller
Journal:  Photochem Photobiol Sci       Date:  2010-10-08       Impact factor: 3.982

9.  Palladium-catalyzed reactions of cyclohexadienones: regioselective cyclizations triggered by alkyne acetoxylation.

Authors:  Rodolfo Tello-Aburto; Andrew M Harned
Journal:  Org Lett       Date:  2009-09-03       Impact factor: 6.005

10.  Copper-free "click" modification of DNA via nitrile oxide-norbornene 1,3-dipolar cycloaddition.

Authors:  Katrin Gutsmiedl; Christian T Wirges; Veronika Ehmke; Thomas Carell
Journal:  Org Lett       Date:  2009-06-04       Impact factor: 6.005

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  4 in total

1.  (3+2)-Cycloaddition Reactions of Oxyallyl Cations.

Authors:  Hui Li; Jimmy Wu
Journal:  Synthesis (Stuttg)       Date:  2015-01       Impact factor: 3.157

Review 2.  Photochemical Approaches to Complex Chemotypes: Applications in Natural Product Synthesis.

Authors:  Markus D Kärkäs; John A Porco; Corey R J Stephenson
Journal:  Chem Rev       Date:  2016-04-27       Impact factor: 60.622

3.  Synthesis of Diverse 11- and 12-Membered Macrolactones from a Common Linear Substrate Using a Single Biocatalyst.

Authors:  Michael M Gilbert; Matthew D DeMars; Song Yang; Jessica M Grandner; Shoulei Wang; Hengbin Wang; Alison R H Narayan; David H Sherman; K N Houk; John Montgomery
Journal:  ACS Cent Sci       Date:  2017-11-15       Impact factor: 14.553

4.  Synthesis of (E,E)-Dienones and (E,E)-Dienals via Palladium-Catalyzed γ,δ-Dehydrogenation of Enones and Enals.

Authors:  Gao-Fei Pan; Xing-Long Zhang; Xue-Qing Zhu; Rui-Li Guo; Yong-Qiang Wang
Journal:  iScience       Date:  2019-09-21
  4 in total

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