Literature DB >> 18336038

Diastereoselective syntheses of chroman spiroketals via [4 + 2] cycloaddition of enol ethers and o-quinone methides.

Maurice A Marsini1, Yaodong Huang, Christopher C Lindsey, Kun-Liang Wu, Thomas R R Pettus.   

Abstract

A variety of chroman spiroketals are synthesized via inverse-demand [4 + 2] cycloaddition of enol ethers and ortho-quinone methides (o-QMs). Low temperature o-QM generation in situ allows for the kinetic, diastereoselective construction of these motifs, providing entry to a number of unusual chroman spiroketal natural products.

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Year:  2008        PMID: 18336038      PMCID: PMC2430732          DOI: 10.1021/ol8003244

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


  13 in total

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2.  Berkelic acid, a novel spiroketal with selective anticancer activity from an acid mine waste fungal extremophile.

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Journal:  J Org Chem       Date:  2006-07-07       Impact factor: 4.354

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Journal:  Org Lett       Date:  2006-06-22       Impact factor: 6.005

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Authors:  H Brockmann; W Lenk; G Schwantje; A Zeeck
Journal:  Tetrahedron Lett       Date:  1966-07       Impact factor: 2.415

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7.  Unusual cycloadditions of o-quinone methides with oxazoles.

Authors:  Christopher C Lindsey; Thomas R R Pettus
Journal:  Tetrahedron Lett       Date:  2006-01-09       Impact factor: 2.415

8.  Diastereoselective dearomatization of resorcinols directed by a lactic acid tether: unprecedented enantioselective access to p-quinols.

Authors:  Lupe H Mejorado; Christophe Hoarau; Thomas R R Pettus
Journal:  Org Lett       Date:  2004-05-13       Impact factor: 6.005

9.  Synthesis of resorcinol derived spironitronates.

Authors:  Maurice A Marsini; Yaodong Huang; Ryan W Van De Water; Thomas R R Pettus
Journal:  Org Lett       Date:  2007-07-24       Impact factor: 6.005

10.  Facile synthesis of naphthoquinone spiroketals by diastereoselective oxidative [3 + 2] cycloaddition.

Authors:  Kun-Liang Wu; Stephanie Wilkinson; Norbert O Reich; Thomas R R Pettus
Journal:  Org Lett       Date:  2007-11-29       Impact factor: 6.005

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  14 in total

1.  A diastereoselective formal synthesis of berkelic acid.

Authors:  Todd A Wenderski; Maurice A Marsini; Thomas R R Pettus
Journal:  Org Lett       Date:  2010-12-07       Impact factor: 6.005

2.  New strategies for natural products containing chroman spiroketals.

Authors:  Jason C Green; G Leslie Burnett; Thomas R R Pettus
Journal:  Pure Appl Chem       Date:  2012       Impact factor: 2.453

3.  Multicomponent Condensation Reactions via ortho-Quinone Methides.

Authors:  Emily E Allen; Calvin Zhu; James S Panek; Scott E Schaus
Journal:  Org Lett       Date:  2017-03-30       Impact factor: 6.005

4.  Evolution of a Strategy for the Enantioselective Total Synthesis of (+)-Psiguadial B.

Authors:  Lauren M Chapman; Jordan C Beck; Caitlin R Lacker; Linglin Wu; Sarah E Reisman
Journal:  J Org Chem       Date:  2018-05-18       Impact factor: 4.354

5.  Synthesis of (-)-berkelic acid.

Authors:  Xiaoxing Wu; Jingye Zhou; Barry B Snider
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

6.  Enantioselective addition of boronates to o-quinone methides catalyzed by chiral biphenols.

Authors:  Yi Luan; Scott E Schaus
Journal:  J Am Chem Soc       Date:  2012-12-03       Impact factor: 15.419

7.  Introduction of the (-)-berkelic acid side chain and assignment of the C-22 stereochemistry.

Authors:  Xiaoxing Wu; Jingye Zhou; Barry B Snider
Journal:  J Org Chem       Date:  2009-08-21       Impact factor: 4.354

8.  Stereoselective synthesis of benzannulated spiroketals: influence of the aromatic ring on reactivity and conformation.

Authors:  Guodong Liu; Jacqueline M Wurst; Derek S Tan
Journal:  Org Lett       Date:  2009-08-20       Impact factor: 6.005

9.  The Generation and Reactions of Quinone Methides.

Authors:  Maria M Toteva; John P Richard
Journal:  Adv Phys Org Chem       Date:  2011-01-01       Impact factor: 2.833

10.  Asymmetric Induction via a Helically Chiral Anion: Enantioselective Pentacarboxycyclopentadiene Brønsted Acid-Catalyzed Inverse-Electron-Demand Diels-Alder Cycloaddition of Oxocarbenium Ions.

Authors:  Chirag D Gheewala; Jennifer S Hirschi; Wai-Hang Lee; Daniel W Paley; Mathew J Vetticatt; Tristan H Lambert
Journal:  J Am Chem Soc       Date:  2018-03-06       Impact factor: 15.419

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