147589-45-5

Upstream product

• 25932-95-0 Ethyl 4-(acetyloxy)-5,8-dimethoxy-2-naphthalenecarboxylate 
• 93-02-7 2,5-dimethoxybenzaldehyde 
• 123-25-1 succinic acid diethyl ester 

Downstream Products

• 500777-04-8 ethyl 4-(benzyloxy)-5,8-dimethoxy-2-naphthoate 
• 464171-71-9 ethyl 5,8-dimethoxy-4-methoxymethoxy-2-naphthoate 

Relevant academic research and scientific papers

Base- and light-assisted synthesis of anthracenes from 3-allylnaphthalene- 2-carbaldehydes

The synthesis of substituted anthracenes from naphthalene precursors is described. The key step involved heating ortho-allyl substituted naphthalene-2-carbaldehydes and potassium t-butoxide in DMF with concomitant irradiation from a high pressure mercury

Regioselective oxidation of 3-monosubstituted juglone derivatives

Derivatives of 3-substituted juglones with either electron-withdrawing or -donating substituents are regioselectively oxidized to o- or p- naphthoquinones using salcomine/air or [bis(trifluoroacetoxy)iodo]benzene, respectively. The structure of the oxidation products was confirmed by chemical transformations. A correlation between chemical shift of the single quinoid proton and the quinone structure was established.

Synthesis and bioevaluation of shikonin derivatives

Background: Ester and amide derivatives of shikonin were synthesized to improve the chemical stability of shikonin. Methods: All synthesized compounds were evaluated for their antiproliferative activity against A549 cell line by SRB assay, and five of them demonstrated comparable cytotoxicity to shikonin. Results and Conclusion: The most potent compound, 22d, was more stable and potent than shikonin.

General synthesis route to benanomicin-pradimicin antibiotics

A general approach to the regio- and stereoselective total synthesis of the benanomicin-pradimicin antibiotics (BpAs) is described. Construction of the aglycon has been achieved by 1)the diastereoselective ring-opening of a biaryl lactone by using (R)-val

Synthesis of hydroxylated naphthoquinone derivatives

The use of the Stobbe condensation for the synthesis of juglone derivatives is presented, together with studies towards their further functionalization. The regiospecific oxidation of the above products to o- or p-naphthoquinones was also investigated. Finally, the preparation of useful intermediates for the synthesis of related natural products such as alkannin and shikonin is proposed. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

Directable regiochemistry in naphthazarins via the use of masked derivatives

The carboethoxynaphthol 3d was converted via salcomine oxidation to the masked carboethoxynaphthazarin 4b which could undergo nucleophilic addition or, if unmasked, transfer quinone reactivity to the alternative ring in form 5. The latter should undergo regiospecific Diels-Alder reactions.