Literature DB >> 22889083

Synthesis of 6,6'-binaphthopyran-2-one natural products: pigmentosin A, talaroderxines A and B.

Charles I Grove1, Michael J Di Maso, Firoz A Jaipuri, Michelle B Kim, Jared T Shaw.   

Abstract

Efficient and stereoselective syntheses of pigmentosin A, talaroderxine A, and its diastereomer talaroderxine B are reported. The binaphthyl ring system is assembled by vanadium-catalyzed phenolic coupling of tricyclic precursors. These key intermediates were prepared by Michael-Dieckmann annulation of a protected orsellinate ester, with the requisite pyranones accessed by a new variant of Ghosez's sulfone-epoxide annulation. Preliminary biological experiments are reported for pigmentosin.

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Year:  2012        PMID： 22889083      PMCID： PMC3461326          DOI： 10.1021/ol301743t

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


  13 in total

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2.  Isolation and structures of antibacterial binaphtho-alpha-pyrones, talaroderxines A and B, from Talaromyces derxii.

Authors:  K Suzuki; K Nozawa; S Nakajima; S Udagawa; K Kawai
Journal:  Chem Pharm Bull (Tokyo)       Date:  1992-05       Impact factor: 1.645

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4.  Total synthesis of (+)-trans-195A.

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5.  Synthesis of (-)-viriditoxin: a 6,6'-binaphthopyran-2-one that targets the bacterial cell division protein FtsZ.

Authors:  Young Sam Park; Charles I Grove; Marcos González-López; Sameer Urgaonkar; James C Fettinger; Jared T Shaw
Journal:  Angew Chem Int Ed Engl       Date:  2011-03-16       Impact factor: 15.336

6.  Fungal bis-Naphthopyrones as Inhibitors of Botulinum Neurotoxin Serotype A.

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Journal:  ACS Med Chem Lett       Date:  2012-04-02       Impact factor: 4.345

7.  Ancistrolikokines A-C: new 5,8'-coupled naphthylisoquinoline alkaloids from Ancistrocladus likoko.

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8.  Synthesis of chiral helical 1,3-oxazines.

Authors:  Harish R Talele; Sibaprasad Sahoo; Ashutosh V Bedekar
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9.  Highly enantioselective oxidative couplings of 2-naphthols catalyzed by chiral bimetallic oxovanadium complexes with either oxygen or air as oxidant.

Authors:  Qi-Xiang Guo; Zhi-Jun Wu; Zhi-Bin Luo; Quan-Zhong Liu; Jian-Liang Ye; Shi-Wei Luo; Lin-Feng Cun; Liu-Zhu Gong
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10.  Stereoselective synthesis of atropisomeric korupensamines A and B utilizing planar chiral arene chromium complex.

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Journal:  J Org Chem       Date:  2004-06-11       Impact factor: 4.354
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  3 in total

1.  Synthesis of stereochemically and skeletally diverse fused ring systems from functionalized C-glycosides.

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Journal:  J Org Chem       Date:  2013-05-21       Impact factor: 4.354

2.  Pigmentosins from Gibellula sp. as antibiofilm agents and a new glycosylated asperfuran from Cordyceps javanica.

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Journal:  Beilstein J Org Chem       Date:  2019-12-16       Impact factor: 2.883

3.  Diastereoselective synthesis of γ- and δ-lactams from imines and sulfone-substituted anhydrides.

Authors:  Nohemy A Sorto; Michael J Di Maso; Manuel A Muñoz; Ryan J Dougherty; James C Fettinger; Jared T Shaw
Journal:  J Org Chem       Date:  2014-03-07       Impact factor: 4.354
  3 in total

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