Literature DB >> 22891882

Cycloaromatization protocol for synthesis of polysubstituted phenol derivatives: method development and mechanistic studies.

William T Spencer1, Alison J Frontier.   

Abstract

The scope of the cycloaromatization of propargylic ethers was explored using operationally simple air- and moisture-insensitive conditions. Highly substituted phenol derivatives were obtained in high yields. Mechanistic experiments indicate that the reaction occurs by an electrocyclization followed by 1,3-proton transfer.

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Year:  2012        PMID: 22891882      PMCID: PMC3448494          DOI: 10.1021/jo3010952

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


  15 in total

1.  Total synthesis of (±)-rocaglamide via oxidation-initiated Nazarov cyclization.

Authors:  John A Malona; Kevin Cariou; William T Spencer; Alison J Frontier
Journal:  J Org Chem       Date:  2012-01-26       Impact factor: 4.354

2.  Enantioselective synthesis of cis-1,2-disubstituted cyclopentanes and cyclohexanes by Suzuki-Miyaura cross-coupling and iridium-catalyzed asymmetric hydrogenation.

Authors:  Andreas Schumacher; Marcus G Schrems; Andreas Pfaltz
Journal:  Chemistry       Date:  2011-11-03       Impact factor: 5.236

3.  Synthesis and SERCA activities of structurally simplified cyclopiazonic acid analogues.

Authors:  Sheng Yao; Daniel Gallenkamp; Katharina Wölfel; Bettina Lüke; Michael Schindler; Jürgen Scherkenbeck
Journal:  Bioorg Med Chem       Date:  2011-06-12       Impact factor: 3.641

4.  Palladium-catalyzed intermolecular decarboxylative coupling of 2-phenylbenzoic acids with alkynes via C-H and C-C bond activation.

Authors:  Congyang Wang; Souvik Rakshit; Frank Glorius
Journal:  J Am Chem Soc       Date:  2010-10-13       Impact factor: 15.419

5.  Sulfur-assisted propargyl-allenyl isomerizations and electrocyclizations for the convenient and efficient synthesis of polyfunctionalized benzenes and naphthalenes.

Authors:  Hongwei Zhou; Yanpeng Xing; Jinzhong Yao; Junhui Chen
Journal:  Org Lett       Date:  2010-08-20       Impact factor: 6.005

6.  Oxidation-initiated Nazarov cyclization of vinyl alkoxyallenes.

Authors:  William T Spencer; Mark D Levin; Alison J Frontier
Journal:  Org Lett       Date:  2010-12-14       Impact factor: 6.005

7.  Sequential pericyclic reaction of ene-diallenes: an efficient approach to the steroid skeleton.

Authors:  Shinji Kitagaki; Kazuhiro Ohdachi; Kumiko Katoh; Chisato Mukai
Journal:  Org Lett       Date:  2006-01-05       Impact factor: 6.005

8.  Site-specific preparation of 2-carboalkoxy-4-substituted naphthalenes and 9-alkylphenanthrenes and evidence for an allene intermediate in the novel base-catalyzed cyclization of 2-alkynylbiphenyls.

Authors:  Yi Wang; Donald J Burton
Journal:  Org Lett       Date:  2006-11-09       Impact factor: 6.005

9.  Nazarov cyclization initiated by peracid oxidation: the total synthesis of (+/-)-rocaglamide.

Authors:  John A Malona; Kevin Cariou; Alison J Frontier
Journal:  J Am Chem Soc       Date:  2009-06-10       Impact factor: 15.419

10.  Palladium-catalyzed tandem reaction of yne-propargylic carbonates with boronic acids: a simple method for the synthesis of fused aromatic rings through allene-mediated electrocyclization.

Authors:  Feng Wang; Xiaofeng Tong; Jiang Cheng; Zhaoguo Zhang
Journal:  Chemistry       Date:  2004-10-25       Impact factor: 5.236

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  1 in total

1.  Facile synthesis of 1,2-dione-containing abietane analogues for the generation of human carboxylesterase inhibitors.

Authors:  Randall J Binder; M Jason Hatfield; Liying Chi; Philip M Potter
Journal:  Eur J Med Chem       Date:  2018-02-19       Impact factor: 6.514

  1 in total

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