The first examples of Cu-catalyzed γ-selective allylic alkenylation using organozinc reagents are reported. (E)-Alkenylzinc iodides were prepared by Fe-catalyzed reductive coupling of terminal arylalkynes with alkyl iodides. In the presence of a copper catalyst, these reagents reacted with allylic bromides derived from Morita-Baylis-Hillman alcohols to give 1,4-dienes in high yields. The reacti...

The plant lipid barriers cuticle and suberin represent one of the largest biological interfaces on the planet. They are comprised of an insoluble polymeric domain with associated organic solvent-soluble waxes. Suberin-associated and plant cuticular waxes contain mixtures of aliphatic components that may include alkyl hydroxycinnamates (AHCs). The canonical alkyl hydroxycinnamates are comprised ...

A highly efficient site-selective desymmetric mono-hydrogenation of 1,4-dienes is reported. This protocol allows rapid access to a wide range chiral allylic alcohols and amides bearing two vicinal centers adjacent the alkene. The utility this method further highlighted by synthesis alkyl side chain zaragozic acid formal total (+)-invictolide.

A glycopolymer carrying trehalose was found to suppress the formation of amyloid fibrils from the amyloid β peptide (1-42) (Aβ), as evaluated by thioflavin T assay and atomic force microscopy. Glycopolymers carrying sugar alcohols also changed the aggregation properties of Aβ, and the inhibitory effect depended on the type of sugar and alkyl side chain. Neutralization activity was confirmed by ...

Cellulose has been directly converted into environmentally friendly alkyl glycoside surfactants in a one pot transformation. By working in ionic liquid media with Amberlyst 15Dry (A15) as catalyst and coupling the rate of cellulose hydrolysis and the rate of glycosidation of the monosaccharides formed with C(4) to C(8) alcohols, it was possible to obtain 82% mass yield of octyl-alpha,beta-gluco...

The copper-catalyzed highly regioselective reaction of internal alkynes with diaryliodonium salts was achieved for the first time. α-Arylketones were obtained in moderate to good yields from arylpropargylic alcohols or aryl alkyl alkynes under mild conditions. It was found that the two kinds of substrates underwent two different arylation-oxygenation pathways under different reaction conditions...

Racemic 1-(β-hydroxypropyl)azoles were prepared by solvent-free direct regioselective ring opening of 1,2-propylene oxide with imidazole or 1,2,4-triazole. Lipase-catalyzed transesterification of alcohols with vinyl acetate resulted in kinetic enantiomers resolution. Separated (S)-enantiomers of (+)-1-(1H-imidazol-1-yl)propan-2-ol and (+)-1-(1H-1,2,4-triazol-1-yl)propan-2-ol were quaternized wi...

The sterols are naturally occurring alcohols which consist basically of the steroid skeleton (cyclopentanoperhydrophenanthrene ring system with two angular methyl groups) and which vary in the number of cyclic double bonds. T o the ring system is attached an alkyl side-chain which also may have double bonds. The conventional representation of the sterol skeleton with numbering is shown in Fig. ...

A direct and scalable route to γ-keto-α,β-unsaturated esters, useful intermediates in medicinal chemistry and natural products synthesis, is reported. The key step involves the use of Grubbs' second-generation olefin metathesis catalyst for cross-metathesis of alkyl acrylates and 2° allylic alcohols. The metathesis step is followed by oxidation to give the desired products in high yield on scal...