Literature DB >> 24171600

Triflic acid-mediated rearrangements of 3-methoxy-8-oxabicyclo[3.2.1]octa-3,6-dien-2-ones: synthesis of methoxytropolones and furans.

Yvonne D Williams1, Christine Meck, Noushad Mohd, Ryan P Murelli.   

Abstract

Methoxytropolones are useful scaffolds for therapeutic development because of their known biological activity and established value in the synthesis of α-hydroxytropolones. Upon treatment with triflic acid, a series of 3-methoxy-8-oxabicyclo[3.2.1]octa-3,6-dien-2-ones rearrange rapidly and cleanly to form methoxytropolones. Interestingly, bicycles that are derived from dimethyl acetylenedicarboxylate (R(2) = R(3) = CO2Me) instead form furans as the major product.

Entities:  

Mesh：

Substances：

Year:  2013        PMID： 24171600      PMCID： PMC3909939          DOI： 10.1021/jo401617r

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


  28 in total

1.  A novel class of zinc-binding inhibitors for the phosphatidylcholine-preferring phospholipase C from Bacillus cereus.

Authors:  S F Martin; B C Follows; P J Hergenrother; C L Franklin
Journal:  J Org Chem       Date:  2000-07-28       Impact factor: 4.354

2.  Total synthesis of anhydrolycorinone utilizing sequential intramolecular Diels-Alder reactions of a 1,3,4-oxadiazole.

Authors:  Scott E Wolkenberg; Dale L Boger
Journal:  J Org Chem       Date:  2002-10-18       Impact factor: 4.354

3.  Photooxygenation of the helimers of (-)-isocolchicine: regio- and facial selectivity of the [4 + 2] cycloaddition with singlet oxygen and surprising endoperoxide transformations.

Authors:  R Brecht; F Büttner; M Böhm; G Seitz; G Frenzen; A Pilz; W Massa
Journal:  J Org Chem       Date:  2001-05-04       Impact factor: 4.354

4.  3-Hydroxy-4-pyrones as Precursors of 4-Methoxy-3-oxidopyridinium Ylides. An Expeditious Entry to Highly Substituted 8-Azabicyclo[3.2.1]octanes.

Authors:  Antonio Rumbo; Antonio Mouriño; Luis Castedo; José L. Mascareñas
Journal:  J Org Chem       Date:  1996-09-06       Impact factor: 4.354

5.  Preferential inhibition of the magnesium-dependent strand transfer reaction of HIV-1 integrase by alpha-hydroxytropolones.

Authors:  Elena A Semenova; Allison A Johnson; Christophe Marchand; David A Davis; Robert Yarchoan; Yves Pommier
Journal:  Mol Pharmacol       Date:  2006-01-17       Impact factor: 4.436

6.  Synthesis, activity, and structural analysis of novel α-hydroxytropolone inhibitors of human immunodeficiency virus reverse transcriptase-associated ribonuclease H.

Authors:  Suhman Chung; Daniel M Himmel; Jian-Kang Jiang; Krzysztof Wojtak; Joseph D Bauman; Jason W Rausch; Jennifer A Wilson; John A Beutler; Craig J Thomas; Eddy Arnold; Stuart F J Le Grice
Journal:  J Med Chem       Date:  2011-06-02       Impact factor: 7.446

7.  Function-oriented synthesis: studies aimed at the synthesis and mode of action of 1alpha-alkyldaphnane analogues.

Authors:  Paul A Wender; Noel D'Angelo; Vassil I Elitzin; Martin Ernst; Eileen E Jackson-Ugueto; John A Kowalski; Sharon McKendry; Markus Rehfeuter; Robert Sun; David Voigtlaender
Journal:  Org Lett       Date:  2007-04-05       Impact factor: 6.005

8.  Structure of HIV-1 reverse transcriptase with the inhibitor beta-Thujaplicinol bound at the RNase H active site.

Authors:  Daniel M Himmel; Karen A Maegley; Tom A Pauly; Joseph D Bauman; Kalyan Das; Chhaya Dharia; Arthur D Clark; Kevin Ryan; Michael J Hickey; Robert A Love; Stephen H Hughes; Simon Bergqvist; Eddy Arnold
Journal:  Structure       Date:  2009-12-09       Impact factor: 5.006

9.  Inhibitors of HIV-1 Reverse Transcriptase-Associated Ribonuclease H Activity.

Authors:  Tatiana Ilina; Krystal Labarge; Stefan G Sarafianos; Rieko Ishima; Michael A Parniak
Journal:  Biology (Basel)       Date:  2012-10-19

10.  Selective inhibition of HIV-1 reverse transcriptase-associated ribonuclease H activity by hydroxylated tropolones.

Authors:  Scott R Budihas; Inna Gorshkova; Sergei Gaidamakov; Antony Wamiru; Marion K Bona; Michael A Parniak; Robert J Crouch; James B McMahon; John A Beutler; Stuart F J Le Grice
Journal:  Nucleic Acids Res       Date:  2005-03-01       Impact factor: 16.971
View more
  20 in total

1.  Efficacy and cytotoxicity in cell culture of novel α-hydroxytropolone inhibitors of hepatitis B virus ribonuclease H.

Authors:  Elena Lomonosova; Jil Daw; Aswin K Garimallaprabhakaran; Nana B Agyemang; Yashkumar Ashani; Ryan P Murelli; John E Tavis
Journal:  Antiviral Res       Date:  2017-06-17       Impact factor: 5.970

2.  Traceless Solid-Phase α-Hydroxytropolone Synthesis.

Authors:  Michael P D'Erasmo; Takashi Masaoka; Jennifer A Wilson; Errol M Hunte; John A Beutler; Stuart F J Le Grice; Ryan P Murelli
Journal:  Medchemcomm       Date:  2016-07-07       Impact factor: 3.597

3.  Synthetic α-Hydroxytropolones as Inhibitors of HIV Reverse Transcriptase Ribonuclease H Activity.

Authors:  Ryan P Murelli; Michael P D'Erasmo; Danielle R Hirsch; Christine Meck; Takashi Masaoka; Jennifer A Wilson; Baofeng Zhang; Rajat K Pal; Emilio Gallicchio; John A Beutler; Stuart F J Le Grice
Journal:  Medchemcomm       Date:  2016-07-07       Impact factor: 3.597

4.  Synthesis of Naturally Occurring Tropones and Tropolones.

Authors:  Na Liu; Wangze Song; Casi M Schienebeck; Min Zhang; Weiping Tang
Journal:  Tetrahedron       Date:  2014-12-09       Impact factor: 2.457

5.  Discovery and Development of a Three-Component Oxidopyrylium [5 + 2] Cycloaddition.

Authors:  Michael P D'Erasmo; Christine Meck; Chad A Lewis; Ryan P Murelli
Journal:  J Org Chem       Date:  2016-04-08       Impact factor: 4.354

6.  Synthetic α-Hydroxytropolones Inhibit Replication of Wild-Type and Acyclovir-Resistant Herpes Simplex Viruses.

Authors:  Peter J Ireland; John E Tavis; Michael P D'Erasmo; Danielle R Hirsch; Ryan P Murelli; Mark M Cadiz; Bindi S Patel; Ankit K Gupta; Tiffany C Edwards; Maria Korom; Eileen A Moran; Lynda A Morrison
Journal:  Antimicrob Agents Chemother       Date:  2016-03-25       Impact factor: 5.191

7.  Hydroxylated tropolones inhibit hepatitis B virus replication by blocking viral ribonuclease H activity.

Authors:  Gaofeng Lu; Elena Lomonosova; Xiaohong Cheng; Eileen A Moran; Marvin J Meyers; Stuart F J Le Grice; Craig J Thomas; Jian-kang Jiang; Christine Meck; Danielle R Hirsch; Michael P D'Erasmo; Duygu M Suyabatmaz; Ryan P Murelli; John E Tavis
Journal:  Antimicrob Agents Chemother       Date:  2014-12-01       Impact factor: 5.191

Review 8.  The hepatitis B virus ribonuclease H as a drug target.

Authors:  John E Tavis; Elena Lomonosova
Journal:  Antiviral Res       Date:  2015-04-08       Impact factor: 5.970

9.  Synthesis of aryl-substituted 2-methoxyphenol derivatives from maltol-derived oxidopyrylium cycloadducts through an acid-mediated ring contraction cascade.

Authors:  Lauren P Bejcek; Ryan P Murelli
Journal:  Chem Commun (Camb)       Date:  2020-02-18       Impact factor: 6.222

10.  The biology and synthesis of α-hydroxytropolones.

Authors:  Christine Meck; Michael P D'Erasmo; Danielle R Hirsch; Ryan P Murelli
Journal:  Medchemcomm       Date:  2014-07-01       Impact factor: 3.597
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.