Literature DB >> 22422638

Arynes and cyclohexyne in natural product synthesis.

Christian M Gampe1, Erick M Carreira.   

Abstract

This Minireview highlights recent advances in the field of aryne and cyclohexyne chemistry that have allowed the extraordinary reactivity of these entities to be harnessed during the course of natural product syntheses. The syntheses presented rely on the use of these reactive species in chemoselective transformations and follow unprecedented synthetic strategies that are inspiring for the practitioners of synthetic organic chemistry.
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2012        PMID: 22422638     DOI: 10.1002/anie.201107485

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  58 in total

1.  A theoretical study of cyclohexyne addition to carbonyl-Cα bonds: allowed and forbidden electrocyclic and nonpericyclic ring-openings of strained cyclobutenes.

Authors:  C Avery Sader; K N Houk
Journal:  J Org Chem       Date:  2012-05-11       Impact factor: 4.354

2.  Expanding the ROMP Toolbox: Synthesis of Air-Stable Benzonorbornadiene Polymers by Aryne Chemistry.

Authors:  Jose M Medina; Jeong Hoon Ko; Heather D Maynard; Neil K Garg
Journal:  Macromolecules       Date:  2017-01-04       Impact factor: 5.985

3.  1,2-Bis(arylthio)arene synthesis via aryne intermediates.

Authors:  Milad Mesgar; Justin Nguyen-Le; Olafs Daugulis
Journal:  Chem Commun (Camb)       Date:  2019-08-07       Impact factor: 6.222

4.  Computational predictions of substituted benzyne and indolyne regioselectivities.

Authors:  Elias Picazo; K N Houk; Neil K Garg
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

5.  Synthesis of Cyclic β-Silylalkenyl Triflates via an Alkenyl Cation Intermediate.

Authors:  Craig J Lee; Manisha Swain; Ohyun Kwon
Journal:  Org Lett       Date:  2018-08-17       Impact factor: 6.005

6.  Synthesis of complex benzenoids via the intermediate generation of o-benzynes through the hexadehydro-Diels-Alder reaction.

Authors:  Beeraiah Baire; Dawen Niu; Patrick H Willoughby; Brian P Woods; Thomas R Hoye
Journal:  Nat Protoc       Date:  2013-02-14       Impact factor: 13.491

7.  A Practical, Multi-gram Synthesis of (±)-Herbindole A, (±)-Herbindole B, and (±)-Herbindole C from a Common Intermediate via 6,7-Indole Aryne Cycloaddition and Pd(0)-Catalyzed Cross-Coupling Reactions.

Authors:  Nalin Chandrasoma; Sivadarshini Pathmanathan; Keith R Buszek
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

8.  Quantification of the Electrophilicity of Benzyne and Related Intermediates.

Authors:  Noah F Fine Nathel; Lucas A Morrill; Herbert Mayr; Neil K Garg
Journal:  J Am Chem Soc       Date:  2016-08-09       Impact factor: 15.419

9.  Safety Assessment of Benzyne Generation from a Silyl Triflate Precursor.

Authors:  Andrew V Kelleghan; Carl A Busacca; Max Sarvestani; Ivan Volchkov; Jose M Medina; Neil K Garg
Journal:  Org Lett       Date:  2020-02-04       Impact factor: 6.005

10.  Generation and regioselective trapping of a 3,4-piperidyne for the synthesis of functionalized heterocycles.

Authors:  Travis C McMahon; Jose M Medina; Yun-Fang Yang; Bryan J Simmons; K N Houk; Neil K Garg
Journal:  J Am Chem Soc       Date:  2015-03-20       Impact factor: 15.419

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