Literature DB >> 12608785

A formal [3 + 3] cycloaddition reaction. Improved reactivity using alpha,beta-unsaturated iminium salts and evidence for reversibility of 6pi-electron electrocyclic ring closure of 1-oxatrienes.

Hong C Shen1, Jiashi Wang, Kevin P Cole, Michael J McLaughlin, Christopher D Morgan, Christopher J Douglas, Richard P Hsung, Heather A Coverdale, Aleksey I Gerasyuto, Juliet M Hahn, Jia Liu, Heather M Sklenicka, Lin-Li Wei, Luke R Zehnder, Craig A Zificsak.   

Abstract

A detailed account regarding a formal [3 + 3] cycloaddition method using 4-hydroxy-2-pyrones and 1,3-diketones is described here. This formal cycloaddition reaction or annulation reaction is synthetically useful for constructing 2H-pyranyl heterocycles. The usage of alpha,beta-unsaturated iminium salts is significant in controlling competing reaction pathways to give exclusively 2H-pyrans. Most significantly, experimental evidence is provided to support the mechanism of this reaction that involves a sequential Knoevenagel condensation and a reversible 6pi-electron electrocyclic ring-closure of 1-oxatrienes.

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Year:  2003        PMID： 12608785     DOI： 10.1021/jo020688t

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


  9 in total

1.  Total synthesis of (±)-phomactin A. Lessons learned from respecting a challenging structural topology.

Authors:  Grant S Buchanan; Kevin P Cole; Yu Tang; Richard P Hsung
Journal:  J Org Chem       Date:  2011-08-05       Impact factor: 4.354

2.  An Enantioselective Synthesis of the ABD Tricycle for (-)-Phomactin A Featuring Rawal's Asymmetric Diels-Alder Cycloaddition.

Authors:  Ling-Feng You; Richard P Hsung; Aaron A Bedermann; Aleksey V Kurdyumov; Yu Tang; Grant S Buchanan; Kevin P Cole
Journal:  Adv Synth Catal       Date:  2008-12-18       Impact factor: 5.837

3.  Aza- and Carbo-[3 + 3] Annulations of Exo-Cyclic Vinylogous Amides and Urethanes. Synthesis of Tetrahydroindolizidines and An Unexpected Formation of Hexahydroquinolines.

Authors:  Sunil K Ghosh; Grant S Buchanan; Quincy A Long; Yonggang Wei; Ziyad F Al-Rashid; Heather M Sklenicka; Richard P Hsung
Journal:  Tetrahedron       Date:  2008-01-28       Impact factor: 2.457

4.  Total synthesis of phomactin A.

Authors:  Yu Tang; Kevin P Cole; Grant S Buchanan; Gang Li; Richard P Hsung
Journal:  Org Lett       Date:  2009-04-02       Impact factor: 6.005

5.  Constructing the Architecturally Distinctive ABD-Tricycle of Phomactin A through an Intramolecular Oxa-[3 + 3] Annulation Strategy.

Authors:  Grant S Buchanan; Kevin P Cole; Gang Li; Yu Tang; Ling-Feng You; Richard P Hsung
Journal:  Tetrahedron       Date:  2011-12-30       Impact factor: 2.457

6.  Total Syntheses of Proposed (±)-Trichodermatides B and C.

Authors:  Qian Li; Yan-Shuang Xu; Gregory A Ellis; Timothy S Bugni; Yu Tang; Richard P Hsung
Journal:  Tetrahedron Lett       Date:  2013-10-09       Impact factor: 2.415

7.  An Enantioselective Synthesis of the ABD Tricycle for (-)-Phomactin A Featuring Rawal's Asymmetric Diels-Alder Cycloaddition.

Authors:  Ling-Feng You; Richard P Hsung; Aaron A Bedermann; Aleksey V Kurdyumov; Yu Tang; Grant S Buchanan; Kevin P Cole
Journal:  Adv Synth Catal       Date:  2008-12-01       Impact factor: 5.837

Review 8.  Recent Advances in the Synthesis of 2H-Pyrans.

Authors:  David Tejedor; Fernando García-Tellado; Samuel Delgado-Hernández; Raquel Diana-Rivero; Abián Díaz-Díaz
Journal:  Molecules       Date:  2019-08-09       Impact factor: 4.411

9.  Eco-friendly synthesis of fused pyrano[2,3-b]pyrans via ammonium acetate-mediated formal oxa-[3 + 3]cycloaddition of 4H-chromene-3-carbaldehydes and cyclic 1,3-dicarbonyl compounds.

Authors:  Vitaly A Osyanin; Dmitry V Osipov; Irina A Semenova; Kirill S Korzhenko; A V Lukashenko; Oleg P Demidov; Yuri N Klimochkin
Journal:  RSC Adv       Date:  2020-09-16       Impact factor: 4.036
  9 in total

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