888958-30-3

Upstream product

• 106-95-6 allyl bromide 
• 154714-19-9 5-hydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one 

Downstream Products

• 74292-73-2 2-allyloxy-6-hydroxybenzoic acid methyl ester 
• 1449336-31-5 (R)-MPA ester of spirooliganone A 
• 1449336-32-6 (S)-MPA ester of spirooliganone A 
• 1449336-36-0 (R)-MPA ester of spirooliganone B 
• 1449336-37-1 (S)-MPA ester of spirooliganone B 
• 1616-51-9 3-allyloxyphenol 

Relevant academic research and scientific papers

Oxidative cyclization of alkenoic acids promoted by AgOAc

Alkenoic acids derived from salicylic acid and analogues undergo an unexpected oxidative cyclization process triggered by AgOAc leading to 4H-benzo[d][1,3]dioxin-4-ones. The process is affected by the substitution on the aryl and the allyl units.

Total Syntheses of (-)-Spirooliganones A and B and Their Diastereoisomers: Absolute Stereochemistry and Inhibitory Activity against Coxsackie Virus B3

To investigate the effects of configuration on bioactivity, spirooliganones A and B and their six diastereoisomers (1-8) were synthesized in 11 steps. The key benzopyran core was assembled by intermolecular [4 + 2] hetero-Diels-Alder cycloaddition between (-)-sabinene and o-quinone methide, which was generated from the corresponding o-hydroxybenzyl alcohol. After establishing the absolute configuration, the inhibitory activities of spirooliganones 1-8 against Coxsackie virus B3 were evaluated, and the primary structure-activity relationships were analyzed. Compound 3 was the most potent compound, with an IC50 of 0.41 μM.

Two axles threaded using a single template site: Active metal template macrobicyclic [3]rotaxanes

Template approaches to rotaxanes normally require at least n - 1 template sites to interlock n components. Here we describe the one-pot synthesis of [3]rotaxanes in which a single metal template site induces formation of axles through each cavity of a bicyclic macrocycle. Central to the approach is that a portion of the bicyclic molecule acts as a ligand for a transition metal ion that mediates covalent bond formation through one or other macrocyclic cavity, depending on the ligand's orientation, making a mechanical bond. The ligand can then rotate so that the transition metal can catalyze the formation of a second axle through the other macrocycle. Using this strategy with the Cu(I)-catalyzed azide-alkyne cycloaddition (the CuAAC reaction) generates a [3]rotaxane with two identical axles in up to 86% yield. [3]Rotaxanes with two different axles threaded through the macrobicyclic rings can also be created using a single template site, either by having copper(I) sequentially form both mechanical bonds (via the CuAAC reaction) using different sets of building blocks for each axle or by using two different reactions catalyzed by two different metal ions: a palladium(II)-mediated alkyne homocoupling to assemble the first thread through one cavity, followed by a copper(I)-mediated CuAAC reaction to form the second axle through the other ring.

Efficient bis-C-aminoglycosylation toward the synthesis of the pluramycins

Two bis-C-aminoglycosyl arenes containing the angolosamine and the vancosamine moieties, which are potentially useful as the D-ring fragments of the pluramycin-type antibiotics, were efficiently synthesized by the OC-glycoside rearrangement based strategy