Literature DB >> 20597470

Synthesis of antimicrobial natural products targeting FtsZ: (+)-totarol and related totarane diterpenes.

Michelle B Kim1, Jared T Shaw.   

Abstract

An efficient, convergent synthesis of totarol by a diastereoselective epoxide/alkene/arene bicyclization is described. The reported synthesis enables the preparation of related diterpenes totaradiol and totarolone as well as previously unavailable derivatives that exhibit comparable inhibition of the bacterial cell division protein FtsZ.

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Year:  2010        PMID: 20597470      PMCID: PMC2927847          DOI: 10.1021/ol100929z

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


  33 in total

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Journal:  Nat Rev Mol Cell Biol       Date:  2005-11       Impact factor: 94.444

Review 3.  Cell-division inhibitors: new insights for future antibiotics.

Authors:  Rowena L Lock; Elizabeth J Harry
Journal:  Nat Rev Drug Discov       Date:  2008-04       Impact factor: 84.694

4.  An inhibitor of FtsZ with potent and selective anti-staphylococcal activity.

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Journal:  Science       Date:  2008-09-19       Impact factor: 47.728

5.  The synthesis and antibacterial activity of totarol derivatives. Part 1: modifications of ring-C and pro-drugs.

Authors:  G B Evans; R H Furneaux; M B Gravestock; G P Lynch; G K Scott
Journal:  Bioorg Med Chem       Date:  1999-09       Impact factor: 3.641

6.  The synthesis and antibacterial activity of totarol derivatives. Part 3: Modification of ring-B.

Authors:  G B Evans; R H Furneaux; G J Gainsford; M P Murphy
Journal:  Bioorg Med Chem       Date:  2000-07       Impact factor: 3.641

7.  Enantioselective halocyclization of polyprenoids induced by nucleophilic phosphoramidites.

Authors:  Akira Sakakura; Atsushi Ukai; Kazuaki Ishihara
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8.  Production of epoxydammaranes by the enzymatic reactions of (3R)- and (3S)-2,3-squalene diols and those of 2,3:22,23-dioxidosqualenes with recombinant squalene cyclase and the mechanistic insight into the polycyclization reactions.

Authors:  Tsutomu Hoshino; Yukie Yonemura; Takamasa Abe; Yumi Sugino
Journal:  Org Biomol Chem       Date:  2007-01-19       Impact factor: 3.876

9.  Indium tribromide-promoted arene-terminated epoxy olefin cyclization.

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Journal:  Chem Commun (Camb)       Date:  2008-01-16       Impact factor: 6.222

10.  Antibacterial activity of anacardic acid and totarol, alone and in combination with methicillin, against methicillin-resistant Staphylococcus aureus.

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  12 in total

1.  Palladium-catalyzed allylic substitution with (η6-arene-CH2Z)Cr(CO)(3)-based nucleophiles.

Authors:  Jiadi Zhang; Corneliu Stanciu; Beibei Wang; Mahmud M Hussain; Chao-Shan Da; Patrick J Carroll; Spencer D Dreher; Patrick J Walsh
Journal:  J Am Chem Soc       Date:  2011-11-29       Impact factor: 15.419

2.  Practical synthesis of PC190723, an inhibitor of the bacterial cell division protein FtsZ.

Authors:  Nohemy A Sorto; Marilyn M Olmstead; Jared T Shaw
Journal:  J Org Chem       Date:  2010-10-29       Impact factor: 4.354

3.  Synthesis of the diaryl ether cores common to chrysophaentins A, E and F.

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4.  The Synthesis and Antimicrobial Activity of Heterocyclic Derivatives of Totarol.

Authors:  Michelle B Kim; Terrence E O'Brien; Jared T Moore; David E Anderson; Marie H Foss; Doug-Las B Weibel; James B Ames; Jared T Shaw
Journal:  ACS Med Chem Lett       Date:  2012-08-28       Impact factor: 4.345

5.  Coupling of sterically hindered trisubstituted olefins and benzocyclobutenones by C-C activation: total synthesis and structural revision of cycloinumakiol.

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6.  Inhibitory effect of totarol on exotoxin proteins hemolysin and enterotoxins secreted by Staphylococcus aureus.

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Journal:  World J Microbiol Biotechnol       Date:  2015-07-21       Impact factor: 3.312

7.  Inhibitors of bacterial tubulin target bacterial membranes in vivo.

Authors:  Marie H Foss; Ye-Jin Eun; Charles I Grove; Daniel A Pauw; Nohemy A Sorto; Jarred W Rensvold; David J Pagliarini; Jared T Shaw; Douglas B Weibel
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8.  Synthesis of a library of "lead-like" γ-lactams by a one pot, four-component reaction.

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9.  Antibacterial activity and mode of action of totarol against Staphylococcus aureus in carrot juice.

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Journal:  J Food Sci Technol       Date:  2018-02-03       Impact factor: 2.701

10.  A Relay Strategy Actuates Pre-Existing Trisubstituted Olefins in Monoterpenoids for Cross-Metathesis with Trisubstituted Alkenes.

Authors:  Karim A Bahou; D Christopher Braddock; Adam G Meyer; G Paul Savage; Zhensheng Shi; Tianyou He
Journal:  J Org Chem       Date:  2020-03-19       Impact factor: 4.354

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