171565-80-3

Upstream product

• 143616-19-7 (S)-dihydro-4-(3,4,5-trimethoxybenzyl)furan-2(3H)-one 
• 167759-92-4 2-bromo-4,5-dimethoxy-3-(4-nitrobenzyloxy)benzaldehyde 
• 99-24-1 methyl galloate 
• 83011-43-2 3-hydroxy-4,5-dimethoxybenzoate 
• 26409-24-5 methyl 3-benzyloxy-4,5-dimethoxybenzoate 
• 79831-86-0 methyl 3-(benzyloxy)-4,5-dihydroxybenzoate 
• 133269-68-8 (S)-3-methoxycarbonyl-4-(3,4,5-trimethoxy-phenyl)butanoic acid 
• 165673-39-2 (E)-3-(methoxycarbonyl)-4-(3,4,5-trimethoxy-phenyl)but-3-enoic acid 
• 236392-94-2 2-bromo-4,5-dimethoxy-3-hydroxybenzoic acid methyl ester 
• 171565-79-0 2-bromo-4,5-dimethoxy-3-(4-nitrobenzyloxy)benzyl alcohol 
• 171565-78-9 methyl 2-bromo-4,5-dimethoxy-3-(4-nitrobenzyloxy)benzoate 

Downstream Products

• 171565-86-9 (R-Biar)-11-benzyloxy-4,13-dihydro-6,7,8,9,10-pentamethoxydibenzo<4,5:6,7>cycloocta<1,2-c>furan-1(3H)-one 

Relevant academic research and scientific papers

Total Syntheses of the Metabolites of Schizandrin

The total syntheses of the metabolites of schizandrin were achieved.The tetracyclic lactone intermediates (13a-e) were prepared in optically pure form by the oxidative coupling reaction of the corresponding 3-benzyl-2-benzylidenebutyrolactones.Mukaiyama hydration of 13b afforded hydroxylactone (14), which was converted into SZ-M3 (4).The introduction of C6,7-diol moiety, which is common to the metabolites (4-11), was carried out by the successive double bond migration to 15a-e, lactone ring reduction ot the allylic diols (32a-e), and glycol formation.Then, reduction of the mesylates 33 completed the syntheses of the metabolites.