Synthesis and biological evaluation of (+/-)-dinemasone C and analogues.

@article{Stewart2010SynthesisAB,
  title={Synthesis and biological evaluation of (+/-)-dinemasone C and analogues.},
  author={Am Stewart and Kathrin Meier and Barbara Joan Schulz and Michael Steinert and Barry B. Snider},
  journal={The Journal of organic chemistry},
  year={2010},
  volume={75 17},
  pages={
          6057-60
        }
}
Dinemasone C was prepared in three steps (8% overall yield) from cis-tetrahydro-4-hydroxy-6-methyl-2-pyrone by aldol reaction with 2,4-hexadienal, epoxidation followed by cyclization, and epimerization of the ring fusion. Dinemasone C, epi-dinemasone C, anhydrodinemasone BC, and nor-dinemasone B are active against bacteria, including Legionella pneumophila Corby, algae, and fungi. 
Concise and direct construction of cis-pyrano[4,3-b]pyran-5-one skeleton from glucal derivatives: synthesis of ent-4-deoxy-2,3-di-epi-dinemasone BC
Abstract (−)-Dinemasones B and C were isolated from a culture of the endophytic fungus Dinemasporium strigosum and had shown attractive antimicrobial activities in vitro. Described herein is theExpand
Stereoselective total synthesis of dinemasone A by double intramolecular hetero-Michael addition (DIHMA).
TLDR
The first total synthesis of dinemasone A, a bioactive metabolite with a spiroketal moiety, is described, which involves a double intramolecular hetero-Michael addition of an ynone moiety. Expand
Total Synthesis and Bioactivity Studies of Fungal Metabolite (-)-TAN-2483B.
TLDR
Inhibition of kinases Btk and Bmx, bacterial priority pathogens, and cytokine production in splenocytes indicates promising therapeutic potential and alkyne functionalization and carbonylation stereoselectively establish the bicyclic core of (-)-TAN-2483B. Expand
Synthesis of Bioactive Side-Chain Analogues of TAN-2483B.
TLDR
A chiral pool approach to this core and prepared side-chain analogues of TAN-2483B showed micromolar activity towards cancer cell lines HL-60, 1A9 and MCF-7 and certain human disease-relevant kinases, including Bruton's tyrosine kinase (Btk). Expand
A carbohydrate-based approach for the total synthesis of (-)-dinemasone B, (+)-4a-epi-dinemasone B, (-)-7-epi-dinemasone B, and (+)-4a,7-Di-epi-dinemasone B.
TLDR
The first total synthesis of (-)-dinemasone B is described, which features a stereoselective reduction of C-glycosidic ketone, lactonization, and E-olefination of aldehyde starting from D-glucose. Expand
Synthesis of β-hydroxy-δ-trichloromethyl-δ-valerolactones by intramolecular samarium/ytterbium diiodide-mediated Reformatsky reaction
The synthesis of α-methyl-β-hydroxy-δ-trichloromethyl - δ-valerolactone was achieved by an intramolecular Reformatsky reaction. The cyclisation was effected by samarium diiodide or (for the firstExpand
3-epi-Waol A and Waol C: polyketide-derived γ-lactones isolated from the endophytic fungus Libertella blepharis F2644
Two new γ-lactones, 3-epi-Waol A (1), and Waol C (2) were isolated, together with three known compounds [1-hydroxy-6-methyl-8-hydroxymethylxanthone, pestacin, and isopestacin], from the solid cultureExpand
Viburspiran, an Antifungal Member of the Octadride Class of Maleic Anhydride Natural Products†
Viburspiran (8), a structurally new member of the maleic anhydride natural products, was isolated, along with seven known compounds 9–15, from the fungal endophyte Cryptosporiopsis sp. The structureExpand
Marrying iterative synthesis to cascading radical cyclization: 6-endo/5-exo radical cascade across bis-vinyl ethers.
TLDR
A cascading 6-endo- trig/5-exo-trig radical cyclization across bis-vinyl ether substrates, which are themselves iteratively synthesized from simple building blocks are described. Expand
Antimicrobial Chemical Constituents from the Endophytic Fungus Phomopsis sp. from Notobasis syriaca
TLDR
A new phomosine derivative has been isolated from Phomopsis sp. Expand
...
1
2
...