77220-15-6

Upstream product

• 106-51-4 p-benzoquinone 
• 3786-46-7 3,6-dihydroxyphthalic acid 
• 4733-50-0 2,3-dicyano-1,4-hydroquinone 
• 77220-06-5 2,5-bis<(trimethylsilyl)oxy>furan 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 65489-47-6 dimethyl 3,6-dimethoxyphthalate 
• 7474-92-2 1,4-dihydroxy-2,3-dicarbomethoxy-benzene 

Downstream Products

• 1206719-53-0 C₁₉H₁₂N₂O₆S₂ 
• 1206719-45-0 C₁₆H₁₉NO₆S₂ 
• 104422-98-2 dimethyl 1,4-dihydroxy-6-methoxy-5,8-bis(phenylmethoxy)-2,3-naphthalenedicarboxylate 
• 104422-91-5 3'-(diethoxymethyl)-3-hydroxy-1',6-dimethoxy-9'-(methoxymethoxy)-4,5,8,9-tetrakis(phenylmethoxy)spiro<2H-benzindene-2,8'-<8H>cyclopentisoquinolin>-1(3H)-one 
• 115757-73-8 3-<3-(diethoxymethyl)-1-methoxy-9-(methoxymethoxy)-8H-cyclopentisoquinolin-8-ylidene>-6-methoxy-4,5,8,9-tetrakis(phenylmethoxy)naphtho<2,3-c>furan-1(3H)-one 
• 104423-03-2 3'-(diethoxymethyl)-1',6-dimethoxy-9'-(methoxymethoxy)-4,5,8,9-tetrakis(phenylmethoxy)spiro<2H-benzindene-2,8'-<8H>cyclopentisoquinoline>-1,3-dione 
• 115796-78-6 3-<3-(diethoxymethyl)-1-methoxy-9-(methoxymethoxy)-8H-cyclopentisoquinolin-8-ylidene>-7-methoxy-4,5,8,9-tetrakis(phenylmethoxy)naphtho<2,3-c>furan-1(3H)-one 
• 104422-99-3 dimethyl 6-methoxy-1,4,5,8-tetrakis(phenylmethoxy)-2,3-naphthalenedicarbocylate 
• 104423-00-9 6-methoxy-4,5,8,9-tetrakis(phenylmethoxy)naphtho<2,3-c>furan-1,3-dione 
• 104422-89-1 1,4,5,8-Tetrakis-benzyloxy-3-{[7-diethoxymethyl-4-methoxymethoxy-5-oxo-5,6-dihydro-6-aza-cyclopenta[b]naphthalen-(3Z)-ylidene]-hydroxy-methyl}-6-methoxy-naphthalene-2-carboxylic acid 
• 104422-88-0 1,4,5,8-Tetrakis-benzyloxy-3-{[7-diethoxymethyl-4-methoxymethoxy-5-oxo-5,6-dihydro-6-aza-cyclopenta[b]naphthalen-(1Z)-ylidene]-hydroxy-methyl}-7-methoxy-naphthalene-2-carboxylic acid 
• 104422-97-1 dimethyl 4-methoxy-3,6-bis(phenylmethoxy)phthalate 
• 103548-64-7 dimethyl 3,4,6-trihydroxyphthalate 
• 103548-65-8 dimethyl 3,6-dihydroxy-4-methoxyphthalate 

Relevant academic research and scientific papers

Bisketene Equivalents as Diels-Alder Dienes

2,5-Bis(tert-butyldimethylsilyloxy)furans are established as vicinal bisketene equivalents for application as dienes in the Diels-Alder reaction. Cycloaddition with olefinic dienophiles, under exceptionally mild conditions, enables convergent access to highly substituted para-hydroquinones in unprotected form via a one-pot Diels-Alder/ring-opening/tautomerization sequence. The synthesis of para-benzoquinones from acetylenic dienophiles, including benzynes, is also demonstrated, and 2,5-bis(tert-butyldimethylsilyloxy)pyrroles are established as competent dienes for the synthesis of para-iminoquinones. Application in natural product synthesis enables gram-scale access to the neuroprotective agent (±)-indanostatin.

Evaluation of some preparations of trialkoxyphthalic acid derivatives

Several approaches to trialkoxyphthalic acid derivatives, potential intermediates in a fredericamycin synthesis, were tested. Sequences based on a Diels-Alder/retro Diels-Alder reaction, a cyanide addition to a quinone, an Elbe oxidation, and an amide-directed ortho-lithiation are discussed in terms of length, yields, convenience, and the versatility of the product of each.

CHEMISTRY OF 2,5-BIS(TRIMETHYLSILOXY)FURANS. I: PREPARATION AND DIELS-ALDER REACTIONS

A number of substituted 2,5-bis(trimethylsiloxy)furans were prepared from the corresponding succinic anhydrides, and were found to be reactive dienes from the Diels-Alder reaction with electron-withdrawing dienophiles, giving p-quinones and hydroquinones.