95712-56-4

Upstream product

• 100-39-0 benzyl bromide 
• 120-80-9 benzene-1,2-diol 
• 6272-38-4 O-benzylcatechol 
• 100-44-7 benzyl chloride 
• 24677-78-9 2,3-dihydroxybenzaldehyde 
• 541-41-3 chloroformic acid ethyl ester 
• 86734-59-0 3-benzyloxy-2-hydroxybenzaldehyde 

Downstream Products

• 95712-54-2 2-hydroxy-3-(benzyloxy)-6-bromobenzaldehyde 
• 61774-75-2 8-(benzyloxy)-7-methoxy-2,3-(methylenedioxy)benzophenanthridine 
• 54354-62-0 decarine 
• 95712-55-3 2-methoxy-3-(benzyloxy)-6-bromobenzaldehyde 
• 113250-87-6 6-Benzyloxy-3-bromo-2-dimethoxymethyl-phenol 
• 113250-74-1 N-(6-bromo-2-methoxy-3-(benzyloxy)benzylidene)-6,7-(methylenedioxy)-1-naphthylamine 
• 95712-58-6 N-<3'-(benzyloxy)-6'-bromo-2'-methoxybenzyl>-6,7-(methylenedioxy)-1-naphthylamine 
• 1442686-52-3 C₂₂H₂₀O₆ 
• 1442686-53-4 C₁₅H₁₃BrO₄ 
• 95712-57-5 Carbonic acid 6-benzyloxy-3-bromo-2-formyl-phenyl ester ethyl ester 

Relevant academic research and scientific papers

Synthesis of 1,7-dimethoxy-2-hydroxyxanthone, a natural product with potential activity on erectile dysfunction

The natural product, 1,7-dimethoxy-2-hydroxyxanthone (1), isolated from Securidaca inappendiculate Hassk, has a potential in the treatment of erectile dysfunction due to its significant relaxation activity on rabbit Corpus cavernosum. However, the isolation of compound 1 is problematic because of its high similarity in structure to its analogs. In this paper, the first synthesis of 1 was reported featuring two key reactions: a copper-catalyzed coupling reaction and an intramolecular cyclization.

Benzyne Cyclization Route to Benzophenanthridine Alkaloids. Synthesis of Chelerythrine, Decarine, and Nitidine

The alkaloids chelerythrine (8b) and decarine (7c) have been synthesized through a benzyne-mediated cyclization of N-(2-halobenzyl)-1-naphthylamines 4 with KNH2 in ammonia/ether.The 7-hydroxybenzophenanthridine structure 16a proposed for the alkaloid fagaridine is questioned on the basis of comparison with a model compound (16b) synthesized by benzyne cyclization.For the 8,9-oxygenated alkaloids like nitidine (8i), this cyclization proceeded poorly, but a dramatic improvement occurred when LDA/THF at -78 deg C was used instead of KNH2/NH3.