Literature DB >> 16869640

Total synthesis of (+/-)-mitorubrinic acid.

Maurice A Marsini1, Kristoffer M Gowin, Thomas R R Pettus.   

Abstract

[reaction: see text] (+/-)-Mitorubrinic acid, a member of the azaphilone family of natural products, has been constructed in 12 steps. Key aspects of the synthesis include elaboration and oxidative dearomatization of an isocoumarin intermediate to provide the azaphilone nucleus with a disubstituted, unsaturated carboxylic acid side chain.

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Year:  2006        PMID： 16869640      PMCID： PMC2440338          DOI： 10.1021/ol0610993

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


  14 in total

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Authors:  Y Tabata; S Ikegami; T Yaguchi; T Sasaki; S Hoshiko; S Sakuma; K Shin-Ya; H Seto
Journal:  J Antibiot (Tokyo)       Date:  1999-04       Impact factor: 2.649

2.  THE STRUCTURES OF MITORUBRIN AND MITORUBRINOL.

Authors:  G BUECHI; J D WHITE; G N WOGAN
Journal:  J Am Chem Soc       Date:  1965-08-05       Impact factor: 15.419

Review 3.  Enzymatic catalysis of the Diels-Alder reaction in the biosynthesis of natural products.

Authors:  Hideaki Oikawa; Tetsuo Tokiwano
Journal:  Nat Prod Rep       Date:  2004-05-03       Impact factor: 13.423

4.  The chemistry of fungi. LXII. The synthesis of ( )-mitorubrin, a metabolite of Penicillium rubrum.

Authors:  R Chong; R W Gray; R R King; W B Whalley
Journal:  J Chem Soc Perkin 1       Date:  1971

5.  Regioselective oxidation of phenols to o-quinones with o-iodoxybenzoic acid (IBX).

Authors:  Derek Magdziak; Andy A Rodriguez; Ryan W Van De Water; Thomas R R Pettus
Journal:  Org Lett       Date:  2002-01-24       Impact factor: 6.005

6.  Synthesis studies toward chloroazaphilone and vinylogous gamma-pyridones: two common natural product core structures.

Authors:  Wan-Guo Wei; Zhu-Jun Yao
Journal:  J Org Chem       Date:  2005-06-10       Impact factor: 4.354

7.  Synthesis of the azaphilones using copper-mediated enantioselective oxidative dearomatization.

Authors:  Jianglong Zhu; Nicholas P Grigoriadis; Jonathan P Lee; John A Porco
Journal:  J Am Chem Soc       Date:  2005-07-06       Impact factor: 15.419

8.  Mitorubrin derivatives on ascomata of some talaromyces species of ascomycetous fungi

Authors: 
Journal:  J Nat Prod       Date:  1999-09       Impact factor: 4.050

9.  (±)-Diinsininone: made nature's way.

Authors:  Carolyn Selenski; Thomas R R Pettus
Journal:  Tetrahedron       Date:  2006-05-29       Impact factor: 2.457

10.  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
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  6 in total

1.  Stereodivergent, Chemoenzymatic Synthesis of Azaphilone Natural Products.

Authors:  Joshua B Pyser; Summer A Baker Dockrey; Attabey Rodríguez Benítez; Leo A Joyce; Ren A Wiscons; Janet L Smith; Alison R H Narayan
Journal:  J Am Chem Soc       Date:  2019-11-06       Impact factor: 15.419

2.  Reengineering an azaphilone biosynthesis pathway in Aspergillus nidulans to create lipoxygenase inhibitors.

Authors:  Amber D Somoza; Kuan-Han Lee; Yi-Ming Chiang; Berl R Oakley; Clay C C Wang
Journal:  Org Lett       Date:  2012-02-01       Impact factor: 6.005

3.  Enantioselective Synthesis of Hydrobenzofuranones Using an Asymmetric Desymmetrizing Intramolecular Stetter Reaction of Cyclohexadienones.

Authors:  Qin Liu; Tomislav Rovis
Journal:  Org Process Res Dev       Date:  2007       Impact factor: 3.317

4.  A new azaphilone, kasanosin C, from an endophytic Talaromyces sp. T1BF.

Authors:  Liang-Qun Li; Yan-Guang Yang; Ying Zeng; Cheng Zou; Pei-Ji Zhao
Journal:  Molecules       Date:  2010-06-01       Impact factor: 4.411

5.  Recent Advances in the Selective Oxidative Dearomatization of Phenols to o-Quinones and o-Quinols with Hypervalent Iodine Reagents.

Authors:  Xiao Xiao; Sarah E Wengryniuk
Journal:  Synlett       Date:  2021-01-14       Impact factor: 2.454

6.  Talaromyces atroroseus, a new species efficiently producing industrially relevant red pigments.

Authors:  Jens C Frisvad; Neriman Yilmaz; Ulf Thrane; Kasper Bøwig Rasmussen; Jos Houbraken; Robert A Samson
Journal:  PLoS One       Date:  2013-12-19       Impact factor: 3.240
  6 in total

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