93092-15-0

Upstream product

• 6948-30-7 5-bromoveratralaldehyde 
• 121-33-5 vanillin 
• 93092-14-9 1-bromo-5-hydroxy-2,3-dimethoxybenzene 
• 2973-76-4 5-bromo-4-hydroxy-3-methoxybenzaldehyde 
• 544-92-3 copper(I) cyanide 

Downstream Products

• 444119-89-5 [6'-hept-6-enyl-2'-methoxy-2,6,4'-tris-(4-methoxybenzyloxy)-biphenyl-4-yl]-methanol 
• 444119-94-2 4'-bromomethyl-2-methoxy-4,2',6'-tris-(4-methoxybenzyloxy)-6-oct-6-ynyl-biphenyl 
• 444119-91-9 [2'-methoxy-2,6,4'-tris-(4-methoxybenzyloxy)-6'-oct-6-ynyl-biphenyl-4-yl]-methanol 
• 444119-60-2 4'-(tert-butyldiphenylsilanyloxymethyl)-6-methoxy-4,2',6'-tris-(4-methoxybenzyloxy)-biphenyl-2-carbaldehyde 
• 444119-97-5 (Z)-3-Methoxy-5,24,25-tris-(4-methoxy-benzyloxy)-tricyclo[20.2.2.0^2,7]hexacosa-1⁽²⁵⁾,2⁽⁷⁾,3,5,11,22⁽²⁶⁾,23-heptaene 
• 444119-72-6 3-methoxy-5,24,25-tris-(4-methoxy-benzyloxy)-tricyclo[20.2.2.0^2,7]hexacosa-1⁽²⁵⁾,2⁽⁷⁾,3,5,22⁽²⁶⁾,23-hexaen-11-yne 
• 444119-73-7 3-methoxy-5,24,25-tris-(4-methoxy-benzyloxy)-tricyclo[20.2.2.0^2,7]hexacosa-1⁽²⁵⁾,2⁽⁷⁾,3,5,22⁽²⁶⁾,23-hexaen-13-yne 
• 444119-67-9 6-hept-6-enyl-2-methoxy-4,2',6'-tris-(4-methoxybenzyloxy)-4'-non-8-enyl-biphenyl 
• 444119-66-8 2-methoxy-4,2',6'-tris-(4-methoxybenzyloxy)-6-pent-4-ynyl-4'-undec-10-enyl-biphenyl 
• 444119-59-9 2-[4'-(tert-butyldiphenylsilanyloxymethyl)-6-methoxy-4,2',6'-tris-(4-methoxybenzyloxy)-biphenyl-2-yl]-4,4-dimethyl-4,5-dihydro-oxazole 
• 444119-63-5 tert-butyl-[2'-methoxy-2,6,4'-tris-(4-methoxybenzyloxy)-6'-pent-4-enyl-biphenyl-4-ylmethoxy]-diphenylsilane 
• 444119-61-3 1-[4'-(tert-butyldiphenylsilanyloxymethyl)-6-methoxy-4,2',6'-tris-(4-methoxybenzyloxy)-biphenyl-2-yl]-pent-4-en-1-ol 
• 444119-68-0 4'-dodec-10-ynyl-6-hex-4-ynyl-2-methoxy-4,2',6'-tris-(4-methoxybenzyloxy)-biphenyl 
• 444119-69-1 4'-dec-8-ynyl-2-methoxy-4,2',6'-tris-(4-methoxybenzyloxy)-6-oct-6-ynyl-biphenyl 

Relevant academic research and scientific papers

Attempt to synthesize 2,3,5,4′-tetrahydroxystilbene derived from 2,3,5,4′-tetrahydroxystilbene-2-O-β-glucoside (THSG)

An attempt to synthesize aglycone 1 derived from 2,3,5,4′-tetrahydroxystilbene-2-O-β-glucoside (THSG) via the Wittig reaction and Mizoroki-Heck reaction is described. In the Wittig protocol, 2,3,5,4′-tetramethoxystilbene 2 was obtained. Additionally, a palladium-catalyzed Mizoroki-Heck reaction strategy yielded 2-aryl-2,3-dihydrobenzofuran 13 instead of derivative 12 in good yield.

Total synthesis of the turrianes and evaluation of their DNA-cleaving properties

The first total synthesis of three naturally occurring cyclophane derivatives belonging to the turriane family of natural products is described. Their sterically hindered biaryl entity is formed by reaction of the Grignard reagent derived from aryl bromide 10 with the oxazoline derivative 18, and the macrocyclic tether of the targets is efficiently forged by ring closing metathesis. While conventional RCM catalyzed by the ruthenium-carbene complexes 33 or 34 invariably leads to the formation of mixtures of both stereoisomers with the undesirable (E)-alkene prevailing, ring closing alkyne metathesis (RCAM) followed by Lindlar reduction of the resulting cycloalkynes 37 and 38 opens a convenient and stereoselective entry into this class of compounds. RCAM can either be accomplished by using the tungsten alkylidyne complex [(tBuO)3W≡CCMe3] or by means of a catalyst formed in situ from [Mo(CO)6] and para-trifluoromethylphenol. The latter method is significantly accelerated when carried out under microwave heating. Furthermore, the judicious choice of the protecting groups for the phenolic-OH functions turned out to be crucial. PMB-ethers were found to be compatible with the diverse reaction conditions en route to 3-5; their cleavage, however, had to be carried out under carefully optimized conditions to minimize competing O-C PMB migration. Turrianes 3-5 are shown to be potent DNA cleaving agents under oxidative conditions when administered in the presence of copper ions.

Synthetic Studies on the Flavone Derivatives. XII. Synthesis of 2',3',5'- and 3',4',5'-Trioxygenated Flavones

Two unusual flavones, 5,5'-dihydroxy-2',3',6,7-tetramethoxyflavone (1) from Gardenia cramerii and 4',5-dihydroxy-3',5',6,7-tetramethoxyflavone (6) from Artemisia mesatlantia, and their position isomers were synthesized to investigate the structural correlation in terms of spectral data.The structure of the flavone from G. cramerii is discussed.Keywords: 5,5'-dihydroxy-2',3',6,7-tetramethoxyflavone; 2',5-dihydroxy-3',5',6,7-tetramethoxyflavone; 5-hydroxy-2',3',5',6,7-pentamethoxyflavone; 3',5-dihydroxy-4',5',6,7-tetramethoxyflavone; 4',5-dihydroxy-3',5',6,7-tetramethoxyflavone; 5-hydroxy-3',4',5',6,7-pentamethoxyflavone.