68486-81-7

Upstream product

• 74994-44-8 (+/-)-1-(4-benzyloxy-3-iodophenyl)-7-(2-benzyloxy-3,4-dimethoxy-5-iodophenyl)heptan-3-ol 
• 74882-35-2 Toluene-4-sulfonic acid 4-(2-benzyloxy-3,4-dimethoxy-phenyl)-butyl ester 
• 74882-08-9 methyl 4-(2-benzyloxy-3,4-dimethoxyphenyl)butanoate 
• 68486-76-0 4-(2-benzyloxy-3,4-dimethoxyphenyl)-1-bromobutane 
• 74893-18-8 4-(2-benzyloxy-3,4-dimethoxyphenyl)butan-1-ol 
• 74882-06-7 methyl 4-(2-hydroxy-3,4-dimethoxyphenyl)butanoate 
• 74882-02-3 methyl 3-(2-hydroxy-3,4-dimethoxybenzoyl)propionate 
• 74882-05-6 4-(2-hydroxy-3,4-dimethoxyphenyl)butanoic acid 
• 634-36-6 1,2,3-trimethoxybenzene 
• 68486-87-3 1-(4-benzyloxy-3-iodophenyl)-7-(2-benzyloxy-3,4-dimethoxy-5-iodophenyl)heptan-3-one 
• 68486-79-3 1-(4-benzyloxyphenyl)-7-(2-benzyloxy-3,4-dimethoxyphenyl)heptan-3-one 

Relevant academic research and scientific papers

Total Syntheses of the meta,meta-Bridged Biphenyls (+/-)-Myricanol and Myricanone, and of an Isomeric Biphenyl Ether, a 14-Oxametaparacyclophane

The oxidative coupling of 1,7-bis(hydroxyphenyl)heptanoids (2a,b) has been investigated: C-C coupling to meta,meta-bridged biaryls was not observed, but with thallium tris(trifluoroacetate) C-O coupling occurred forming a 14-oxametaparacyclophane analogous to the natural phenols acerogenin-A and galeon.Intramolecular reductive coupling, using tetrakis(triphenylphosphine)nickel(0), of the bis-iodides (11a,b) derived from phenols (2a,b), leads, after deprotection, to the desired meta,meta-bridged biphenyls myricanone and (+/-)-myricanol, albeit in rather low yield.OO-Dimethylmyricanone and (+/-)-OO-dimethylmyricanol were similarly synthesized.Irradiation (254 nm) in alkaline ethanol of the bromides (11g,h) also induced aryl-aryl coupling to form dibenzylmyricanone and (+/-)-dibenzylmyricanol acetate respectively.

Methods for the Construction of Linear 1,7-Diarylheptanoids; Synthesis of Di-O-methylcentrolobol and Precursors (Synthetic and Biosynthetic) to the meta,meta-Bridged Biphenyls Myricanol and Myricanone

1,7-diarylheptanoids are a varied natural product class in which 'linear' types appear to be biosynthetic precursors to macro(carbo)cyclic (3), macro(oxa)cyclic (4), and condensed polycyclic (5) examples.Various methods (suitable for radiolabelling) are described for constructing 'linear' diarylheptanoids, including Grignard couplings (employing activated magnesium) with arylpropanals and oxazonium salts (11a), (11h), (15a), and (15b)> and dithian alkylation (15c)>.Alkyl-lithium treatment of the benzyloxydithian (19b) gave 1,2,3-triphenylcyclopropane.Syntheses via trialkylcyanoborates were frustrated by disproportionation of the intermediate trialkylboranes.The diarylheptanoids synthesised (11a-h) and (15a-e) include synthetic and biosynthetic precursors to meta,meta-bridged biphenyls and related macrocyclic ethers.