An Enantioselective Approach to Furanoeremophilanes: (+)‑9‑Oxoeuryopsin

An enantioselective total synthesis of the furanoeremophilane sesquiterpene (+)-9-oxoeuryopsin <b>1</b> is reported. The synthesis involves as a key step a copper­(II) triflate catalyzed tandem asymmetric conjugate addition of AlMe₃ to 2-methyl-2-cyclohexen-1-one with the Feringa (<i>S</i>,<i>R,R</i>)-phosphoramidite binaphthol ligand, followed by aldol condensation of the resulting aluminum enolate with 4-methyl-3-furaldehyde <b>4</b>. This tandem transformation has not been previously reported with a 2-substituted-2-cyclohexen-1-one. Conventional functional group manipulations completed the synthesis

An Enantioselective Approach to Furanoeremophilanes: (+)‑9‑Oxoeuryopsin

An enantioselective total synthesis of the furanoeremophilane sesquiterpene (+)-9-oxoeuryopsin <b>1</b> is reported. The synthesis involves as a key step a copper­(II) triflate catalyzed tandem asymmetric conjugate addition of AlMe₃ to 2-methyl-2-cyclohexen-1-one with the Feringa (<i>S</i>,<i>R,R</i>)-phosphoramidite binaphthol ligand, followed by aldol condensation of the resulting aluminum enolate with 4-methyl-3-furaldehyde <b>4</b>. This tandem transformation has not been previously reported with a 2-substituted-2-cyclohexen-1-one. Conventional functional group manipulations completed the synthesis

An Enantioselective Approach to Furanoeremophilanes: (+)‑9‑Oxoeuryopsin

An enantioselective total synthesis of the furanoeremophilane sesquiterpene (+)-9-oxoeuryopsin <b>1</b> is reported. The synthesis involves as a key step a copper­(II) triflate catalyzed tandem asymmetric conjugate addition of AlMe₃ to 2-methyl-2-cyclohexen-1-one with the Feringa (<i>S</i>,<i>R,R</i>)-phosphoramidite binaphthol ligand, followed by aldol condensation of the resulting aluminum enolate with 4-methyl-3-furaldehyde <b>4</b>. This tandem transformation has not been previously reported with a 2-substituted-2-cyclohexen-1-one. Conventional functional group manipulations completed the synthesis

An Enantioselective Approach to Furanoeremophilanes: (+)‑9‑Oxoeuryopsin

An enantioselective total synthesis of the furanoeremophilane sesquiterpene (+)-9-oxoeuryopsin <b>1</b> is reported. The synthesis involves as a key step a copper­(II) triflate catalyzed tandem asymmetric conjugate addition of AlMe₃ to 2-methyl-2-cyclohexen-1-one with the Feringa (<i>S</i>,<i>R,R</i>)-phosphoramidite binaphthol ligand, followed by aldol condensation of the resulting aluminum enolate with 4-methyl-3-furaldehyde <b>4</b>. This tandem transformation has not been previously reported with a 2-substituted-2-cyclohexen-1-one. Conventional functional group manipulations completed the synthesis

Tandem Michael addition–Claisen-type condensation of anions of <i>O</i>-ethyl carbonates of cyanohydrins to cyclohex-2-en-1-one

<p>A one pot method for the synthesis of ethyl 2-acetoxy-6-aroylcyclohex-1-ene-1-carboxylates and ethyl 2-acetoxy-6-heterocarbonylcyclohex-1-ene-1-carboxylates through Michael addition of the anions of ethyl carbonates of cyanohydrins to cyclohex-2-en-1-one and subsequent reaction with acetic anhydride is described. These compounds are potential intermediates for the synthesis of 9,10-anthraquinone and heterofused 1,4-naphthoquinone derivatives.</p

Antimicrobial activity and quorum sensing inhibition tests for bioactivity results of 24 <i>Actinobacteria</i> strains.

<p><b>(A1)</b> Picture of <i>Burkholderia</i> spp. phytopathogens without confrontation (Bg: <i>Burkholderia glumae</i>. Bgl: <i>Burkholderia gladioli</i>; Bpl: <i>Burkholderia plantarii</i>). (<b>A2)</b> Picture of confrontation test of <i>Burkholderia</i> spp. phytopathogens against strain number 9. (<b>B1)</b> Picture of <i>Chromobacterium violaceum</i>. (<b>B2)</b> Picture of quorum quenching test against strain number 46b. (<b>C1)</b>. Picture of <i>Fusarium oxysporum f</i>. <i>sp dianthi</i> race 2 against strain 5. (<b>D)</b> Heat map of bioactivity for the 24 strains and their organic extracts. Results for antibacterial, antifungal and QQ activities are summarized in Fig 2D. Horizontal axis shows the codes of the 24 <i>Actinobacteria</i> and vertical axis shows each one of the pathogens tested in both, direct confrontation and extract growth inhibition test. Color indicates the total or partial control of each phytopathogen, assumed as a positive result.</p

Dereplication.

<p>Data for 12 VIPs for quorum quenching activity using Antimarinee database.</p

Strain higher biological activity–HCA- OUT.

<p>Strain higher biological activity–HCA- OUT.</p

Comparison of a phylogenetic reconstruction based on 16S rRNA genes of the actinobacterial isolates and MALDI-TOF profiles clustering.

<p>A Neighbor Joining phylogenetic tree based on 16S rRNA genes of the actinobacterial isolates and their closest relatives (cultivable and uncultivable) was done (left side). Bootstrap calculation was done (1000 repetitions) and is show for the main branches in the tree. A dendrogram based on MALDI-TOF profiles of each isolate (right side) was calculated to compare the obtained results by these two methodologies of classification.</p

Barcoding vs. Phylogenetic tree.

<p>Barcoding based on variables (retention time and <i>m/z</i>) displaying distinct metabolic profiles among the 24 <i>Actinobacteria</i>. Horizontal axis shows variables expressed as <i>m/z</i> values >200 of the 24 extracts. Each variable represents a single compound and its presence is represented by black squares and vertical axis shows each one of <i>Actinobacteria</i> strains according to phylogenetic tree.</p