65857-83-2

Basic information

• Product Name: 8,10-bis(benzyloxy)-11-hydroxy-3-methoxy-1-methylbenzoxanthen-12-one

Upstream product

• 65857-81-0 1,3-bis(benzyloxy)-7-(2-benzyloxy-4-methoxy-6-methylbenzoyl)-6-(2-benzyloxy-4-methoxy-6-methylbenzoyloxy)-8-hydroxynaphthalene 
• 65857-78-5 methyl 2-acetyl-3,5-bis(benzyloxy)phenylacetate 
• 71741-18-9 6,8-Bis-benzyloxy-naphthalene-1,3-diol 
• 52144-91-9 3,5-bis(benzyloxy)diazoacetophenone 
• 65857-79-6 2-benzyloxy-4-methoxy-6-methylbenzyl chloride 
• 79762-35-9 methyl 2-(3,5-bis(benzyloxy)-2-formylphenyl)acetate 
• 100-39-0 benzyl bromide 
• 28917-44-4 3,5-dibenzyloxylbenzoyl chloride 
• 50513-72-9 (3,5-di-benzyloxy)benzoic acid benzyl ester 
• 68048-09-9 2-benzyloxy-4-methoxy-6-methylbenzoic acid 
• 68048-10-2 benzyl 2-benzyloxy-4-methoxy-6-methylbenzoate 
• 65857-80-9 1,3-bis(benzyloxy)-6,8-bis-(2-benzyloxy-4-methoxy-6-methylbenzoyloxy)naphthalene 
• 570-10-5 2-hydroxy-4-methoxy-6-methylbenzoic acid 
• 28917-43-3 3,5-dibenzyloxybenzoic acid 

Downstream Products

• 33390-21-5 bikaverin 
• 33390-22-6 norbikaverin 
• 65857-84-3 8,10-bis(benzyloxy)-3-methoxy-1-methylbenzoxanthen-6,11,12-trione 

Relevant articles and documents

Synthesis of Bikaverin

The total synthesis of bikaverin (1b) is described, from everninic acid (5) and 3,5-dihydrobenzoic acid (6).Dieckmann condensation of methyl 2-acetyl-3,5-bis(benzyloxy)phenylacetate (14), synthesised from (6), followed by treatment with protected everninic acid chloride (9) gave 1,3-bisbenzyloxy-6,8-bis(2-benzyloxy-4-methoxy-6-methylbenzyloxy)naphthalene (16).Photoinduced Fries rearrangement of (16) afforded 1,3-bis(benzyloxy)-7-(2-benzyloxy-4-methoxy-6-methylbenzoyl)-6-(2-benzyloxy-4-methoxy-6-methylbenzoyloxy)-8-hydroxynaphthalene (23).Ring closure of (23) with tetramethylammonium hydroxide in pyridine gave the angular benzoxanthene, 1,3-bis(benzyloxy-6-hydroxy)-10-methoxy-8-methylbenzoxanthen-7-one (25), which was oxidized with potassium dichromate to give the orthoquinone, 1,3-bis(benzyloxy)-10-methoxy-8-methylbenzoxanthen-5,6,7-trione (28).By a novel type of rearrangement, (28) was transformed into the linear benzoxanthen, 8,10-bis(benzyloxy)-3-methoxy-1-methylbenzoxanthen-6,11,12-trione (29) by treatment with silica gel.Oxidation and debenzylation of (29) with manganese dioxide in concentrated H2SO4 gave norbikaverin (1a).