126922-34-7

Upstream product

• 67-56-1 methanol 
• 75445-66-8 8-(benzyloxy)-1-hydroxy-4-methoxynaphthalene 
• 481-39-0 5-hydroxynaphtho-1,4-quinone 
• 75445-68-0 5-Benzyloxy-naphthalene-1,4-diol 
• 175358-83-5 8-(benzyloxy)-1-formyl-4-methoxynaphthalene 
• 100-39-0 benzyl bromide 
• 67243-03-2 5-hydroxy-1-methoxy-4-naphthalenecarboxaldehyde 
• 141812-21-7 1-benzyloxy-5,8-dihydro-5,5,8,8-tetramethoxy-naphthalene 
• 75445-61-3 5-(benzyloxy)-1,4-dihydronaphthalene-1,4-dione 

Downstream Products

• 126922-35-8 8-Benzyloxy-3-[2-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-6-methoxy-4-methyl-phenyl]-4,4-dimethoxy-3,4-dihydro-2H-naphthalen-1-one 
• 175358-99-3 8-Benzyloxy-7-hydroxy-5-methoxy-2-trimethylsilanyl-1,12-dioxa-cyclopenta[a]chrysen-13-one 

Relevant academic research and scientific papers

Synthesis of defucogilvocarcin V isosteres via MAD-mediated conjugate addition of carbanions to naphthoquinone ketals

Treatment of a complex between naphthoquinone ketal 7 and methylaluminum bis(2,6-di-tert-butyl-4-methylphenoxide (MAD) with aryllithium reagents prepared by metallation of oxazoline 13 and amide 18, gave conjugate adducts which were converted to defucogilvocarcin V analogs 2 and 3 via a short reaction sequence. Some problems encountered in the metallation of oxazoline 19, a structural analog of amide 18, are also described.

Anodic Oxidation as a Synthetic Expedient to Naphthoquinone and Anthraquinone Ketals

Some naphthoquinone and anthraquinone ketals have been prepared by anodic oxidation.Regioselective hydrolysis of the above diketals into monoketals is also described.Diels-Alder reaction of (E)-1-methoxybuta-1,3-diene with the monoketal of 1,4-dihydro-4,4-dimethoxy-5-benzyloxynaphthalene proceeded in a regioselective manner. Key words: naphthoquinone ketals, anthraquinone ketals, regioselective hydrolysis, Diels-Alder reaction.

A New Synthesis of Defucogilvocarcin M

A convergent synthesis of the title compound is described.The synthesis revolves around a MAD-mediated coupling of oxazoline 11 and naphthoquinone ketal 16 and requires eight steps via the longest linear sequence.