121668-66-4

Upstream product

• 61550-02-5 (furan-2-yloxy)-trimethylsilane 
• 66-25-1 hexanal 

Relevant academic research and scientific papers

Silica sulfuric acid as a reusable heterogeneous catalyst for the diastereoselective Mukaiyama aldol reaction of 2-(trimethylsilyloxy)furan: Facile synthesis of γ-butenolides

Silica sulfuric acid was found to be an efficient catalyst for the vinylogous Mukaiyama aldol reaction of 2-(trimethylsilyloxy)furan with various aldehydes with good diastereoselection. The reaction proceeds rapidly in THF, affording the corresponding 5-(arylhydroxymethyl)furan-2(5H)-ones in good yields. This method offers significant advantages such as experimental simplicity, and recoverability and reusability of the catalyst.

Tmsi-promoted diastereoselective synthesis of 5-(1'-Hydroxy)-γ- butyrolactones

Trimethylsilyl iodide (TMSI) was found to be an efficient catalyst for the vinylogous Mukaiyama aldol reaction of 2-(trimethylsilyloxy)furan with various aldehydes with good diastereoselection. The reaction proceeds rapidly in CH 2Cl2 affording the corresponding 5-(hydroxy(aryl)methyl) furan-2(5H)-ones in good yields. This method offers significant advantages such as efficiency, generality, and mild reaction conditions with shorter reaction time. Copyright

Synthesis of furanone-based natural product analogues with quorum sensing antagonist activity

The synthesis of 5- and 3-(1′-hydroxyalkyl)-substituted 5H-furan-2-ones 4a-d and 8a-d as well as 5-alkylidene-5H-furan-2-ones 5a-d is described. A study of the structure-activity relationship of these furanone-based natural product analogues towards two different quorum sensing systems is reported. Although the synthesized compounds are not as potent quorum sensing inhibitors as some natural counterparts and a synthetic analogue hereof, interesting structure-activity relationships are seen.

Study of the structure-activity relationships of the acetogenin of annonaceae, muricatacin and analogues

A study of the structure-cytotoxic activity of the acetogenin of Annonaceae, muricatacin 1, is reported. indeed, muricatacin 1 has shown promising antitumoral activity. Therefore several 5-hydroxy-4-alkcanolides were prepared and then tested against KB and VERO cell lines. A few other analogues were synthesized and tested against both cell lines. Thus this work allowed us to better determine the pharmacophore of the molecule and to propose muricatacin 1 instead of a more complicated acetogenin of Annonaceae as a lead compound in the search for new antineoplastic agents.

DIASTEREOSELECTIVITY IN THE DIRECTED ALDOL CONDENSATION OF 2-TRIMETHYLSILOXYFURAN WITH ALDEHYDES. A STEREODIVERGENT ROUTE TO THREO AND ERYTHRO δ-HYDROXY-γ-LACTONES

Threo and erythro-δ-hydroxy-4a,β-unsaturated γ-lactones are obtained with useful diastereoselection by condensing 2-trimethylsiloxyfuran and aldehydes by variying the reaction conditions.A stereomechanistic rationale is presented together with a practical two-step synthesis of the threo and erythro 5-hydroxy-4-decanolides (L-factors).