Literature DB >> 24219829

Synthesis of the tetracyclic core of exiguaquinol.

Gregg M Schwarzwalder1, Sarah E Steinhardt, Hung V Pham, K N Houk, Christopher D Vanderwal.   

Abstract

A Diels-Alder reaction, a desymmetrizing aldol reaction, and a reductive Heck cyclization are employed in a short synthesis of a tetracycle relevant to exiguaquinol, a potential antibiotic. Ground-state energies of this advanced model system and the natural product rationalize the incorrect hemiaminal configuration experimentally obtained and point to the importance of the sulfonate in dictating the relative configuration of the natural product.

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Year:  2013        PMID： 24219829      PMCID： PMC3946388          DOI： 10.1021/ol402905n

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


  6 in total

1.  Asymmetric total synthesis of the proposed structure of the medicinal alkaloid jamtine using the chiral base approach.

Authors:  Nigel S Simpkins; Christopher D Gill
Journal:  Org Lett       Date:  2003-02-20       Impact factor: 6.005

2.  Derivatives of 2,3-anhydro-DL-threitol, 2,3-anhydroerythritol, 2,3:4,5-dianhydrogalactitol, and 2,3:4,5-dianhydroallitol.

Authors:  G Schneider; T Horváth; P Sohár
Journal:  Carbohydr Res       Date:  1977-06       Impact factor: 2.104

Review 3.  Helicobacter pylori: gastric cancer and beyond.

Authors:  D Brent Polk; Richard M Peek
Journal:  Nat Rev Cancer       Date:  2010-06       Impact factor: 60.716

Review 4.  Contiguous stereogenic quaternary carbons: a daunting challenge in natural products synthesis.

Authors:  Emily A Peterson; Larry E Overman
Journal:  Proc Natl Acad Sci U S A       Date:  2004-07-01       Impact factor: 11.205

5.  Exiguaquinol: a novel pentacyclic hydroquinone from Neopetrosia exigua that inhibits Helicobacter pylori MurI.

Authors:  Priscila de Almeida Leone; Anthony R Carroll; Leanne Towerzey; Gordon King; Bernadette M McArdle; Gunther Kern; Stewart Fisher; John N A Hooper; Ronald J Quinn
Journal:  Org Lett       Date:  2008-05-20       Impact factor: 6.005

6.  Palladium-catalyzed asymmetric allylic alkylation of meso- and dl-1,2-divinylethylene carbonate.

Authors:  Barry M Trost; Aaron Aponick
Journal:  J Am Chem Soc       Date:  2006-03-29       Impact factor: 15.419
  6 in total
  2 in total

1.  Strategies for the Synthesis of the Halenaquinol and Xestoquinol Families of Natural Products.

Authors:  Gregg M Schwarzwalder; Christopher D Vanderwal
Journal:  European J Org Chem       Date:  2017-02-16

2.  A Synthesis of Exiguaquinol Dessulfate.

Authors:  Gregg M Schwarzwalder; David R Scott; Christopher D Vanderwal
Journal:  Chemistry       Date:  2016-10-26       Impact factor: 5.236
  2 in total

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