Literature DB >> 14535747

Formal [3 + 3] cycloaddition approach to chromenes and chromanes. Concise total syntheses of (+/-)-rhododaurichromanic acids A and B and methyl (+/-)-daurichromenic ester.

Aleksey V Kurdyumov1, Richard P Hsung, Kirsten Ihlen, Jiashi Wang.   

Abstract

[reaction: see text] Total syntheses of (+/-)-rhododaurichromanic acids A and B and methyl (+/-)-daurichromenic ester are described here. Despite the complex appearances of these compounds, their syntheses are completed in six steps with a 15% overall yield as a mixture by featuring our formal oxa-[3 + 3] cycloaddition methodology.

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Year:  2003        PMID： 14535747     DOI： 10.1021/ol030100k

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


  10 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.  Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions.

Authors:  Saner Poplata; Andreas Tröster; You-Quan Zou; Thorsten Bach
Journal:  Chem Rev       Date:  2016-03-28       Impact factor: 60.622

4.  Convergent Synthesis of 2H-Chromenes - a Formal [3+3] Cycloaddition by a One-pot, Three-Step Cascade.

Authors:  Kathlyn A Parker; Thomas L Mindt
Journal:  Tetrahedron       Date:  2011-12-23       Impact factor: 2.457

5.  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

6.  Synthesis of (-)-Hebelophyllene E: An Entry to Geminal Dimethyl-Cyclobutanes by [2+2] Cycloaddition of Alkenes and Allenoates.

Authors:  Johannes M Wiest; Michael L Conner; M Kevin Brown
Journal:  Angew Chem Int Ed Engl       Date:  2018-03-24       Impact factor: 15.336

7.  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

8.  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

9.  Gold(I)-catalyzed hydroarylation reaction of aryl (3-iodoprop-2-yn-1-yl) ethers: synthesis of 3-iodo-2H-chromene derivatives.

Authors:  Pablo Morán-Poladura; Eduardo Rubio; José M González
Journal:  Beilstein J Org Chem       Date:  2013-10-16       Impact factor: 2.883

10.  Bioactive chemical constituents from the brown alga Homoeostrichus formosana.

Authors:  Hui-Yu Fang; Uvarani Chokkalingam; Shu-Fen Chiou; Tsong-Long Hwang; Shu-Li Chen; Wei-Lung Wang; Jyh-Horng Sheu
Journal:  Int J Mol Sci       Date:  2014-12-30       Impact factor: 5.923
  10 in total

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