As a principal compound of cinnamon essential oil, cinnamaldehyde has been used as marker for the quality control and its oil. During HPLC analysis, reaction product was observed in methanol solution reference standard. This isolated identified to be dimethyl acetal based on spectroscopic analysis. Although dimethylacetalization MeOH recorded many literatures, this is first report about normal ...

The hepatotoxic effects induced by 1,1-dichloroethylene (DCE) are ascribed to cytochrome P-450 (CYP) 2E1-dependent formation of metabolites including 2,2-dichloroacetaldehyde and the DCE-epoxide. The DCE metabolites detected in incubations of liver microsomes are the acetal, the hydrate of 2,2-dichloroacetaldehyde, and the epoxide-derived GSH conjugates 2-S-glutathionyl acetyl glutathione ([B])...

A remarkable double [3 + 2] photocycloaddition reaction that results in the formation of fenestrane 2 from aromatic acetal 1 is reported. During the formation of 2, four carbon-carbon bonds, five new rings, and seven new stereocenters are created in a one-pot process. The reaction occurs in a sequential manner from the linear meta photocycloadduct 3, while the angular meta photocycloadduct 4 un...

In the presence of TMSOTf and a trialkylamine base, acetic acid undergoes aldol addition to non-enolizable aldehydes under exceptionally mild conditions. Acidic workup yields the beta-hydroxy carboxylic acid. The reaction appears to proceed via a three-step, one-pot process, including in situ trimethylsilyl ester formation, bis-silyl ketene acetal formation, and TMSOTf-catalyzed Mukaiyama aldol...

A solution-phase automated synthesis of the versatile synthetic intermediate, Garner's aldehyde, was demonstrated. tert-Butoxycarbonyl (Boc) protection, acetal formation, and reduction of the ester to the corresponding aldehyde were performed utilizing our originally developed automated synthesizer, ChemKonzert. The developed procedure was also useful for the synthesis of Garner's aldehyde anal...

We demonstrate a novel system that exhibits both self-propelled motion and division of micrometer-sized oil droplets induced by chemical conversion of the system components. Such unique dynamics were observed in an oil-in-water emulsion of a benzaldehyde derivative, an alkanol and a cationic surfactant at a low pH.

The enantioselective total synthesis of pironetin has been achieved in 11 steps from known aldehyde 2. The synthesis relies on the formation of 5 out of 6 stereocenters through titanium mediated iterative aldol reactions. Key steps in this synthesis include an acetal aldol reaction to establish the stereochemistry at C8 and C9, an acetate aldol reaction, and "Evans" syn aldol reaction.

Periploside A is a pregnane hexasaccharide identified from the Chinese medicinal plant Periploca sepium, which features a unique seven-membered formyl acetal bridged orthoester (FABO) motif and potent immunosuppressive activities. Here, we show the synthesis of this molecule in a total of 76 steps with the longest linear sequence of 29 steps and 9.2% overall yield. The FABO motif is constructed...

A concise approach to the algal metabolite 1 is described, which also determines the previously unknown stereostructure of this natural product. Compound 1 is distinguished by a rare brominated 4-pyrone nucleus linked as a ketene-acetal to a polyunsaturated macrocyclic scaffold comprising an extra homoallylic bromide entity. The synthesis of 1 is based on the elaboration and selective functiona...