105103-87-5

Upstream product

• 19676-67-6 2,4-dimethoxy-3-methylphenol 
• 5673-07-4 2,6-dimethoxytoluene 
• 518335-54-1 propionic acid 5-bromo-2,4-dimethoxy-3-methylphenyl ester 
• 28006-93-1 5-bromo-2,4-dimethoxy-3-methylbenzaldehyde 
• 7149-92-0 2,4-dimethoxy-3-methylbenzaldehyde 
• 383187-30-2 propionic acid 2,4-dimethoxy-3-methylphenyl ester 

Downstream Products

• 105103-92-2 5-bromo-2,4-dimethoxy-3-methylphenyl <1,1-(2)H2>-2,4-pentadienyl ether 
• 105104-11-8 1-Bromo-2,4-dimethoxy-5-methoxymethoxy-3-methyl-benzene 
• 105104-25-4 5-bromo-2,4-dimethoxy-3-methylphenyl 2,4-hexadienyl ether 
• 1002095-50-2 C₃₉H₄₆N₂O₈ 
• 1002095-35-3 C₃₉H₄₄N₂O₈ 
• 1002095-37-5 C₅₅H₆₈N₄O₁₂S 
• 1002095-31-9 C₃₄H₄₄N₂O₇ 
• 1002095-33-1 C₄₂H₅₀N₂O₈ 
• 1310357-07-3 C₄₉H₅₃F₃N₂O₁₀ 
• 1310357-08-4 C₄₉H₅₃F₃N₂O₁₀ 
• 185981-82-2 1-(benzyloxy)-5-bromo-2,4-dimethoxy-3-methylbenzene 
• 116589-11-8 Methanesulfonic acid (1R,2R,9S,9aS)-5,8-bis-benzyloxy-9-benzyloxymethyl-2-(dimethoxy-phosphorylamino)-7-methoxy-6-methyl-2,3,9,9a-tetrahydro-1H-pyrrolo[1,2-a]indol-1-yl ester 
• 116589-12-9 C₃₇H₄₁N₂O₇P 
• 116589-08-3 Methanesulfonic acid (1R,2S,9S,9aS)-5,8-bis-benzyloxy-9-benzyloxymethyl-1-hydroxy-7-methoxy-6-methyl-2,3,9,9a-tetrahydro-1H-pyrrolo[1,2-a]indol-2-yl ester 

Relevant academic research and scientific papers

Stepwise mechanism for the bromination of arenes by a hypervalent iodine reagent

A mild, metal-free bromination method of arenes has been developed using the combination of bis(trifluoroacetoxy)iodobencene and trimethylsilyl bromide. In situ-formed dibromo(phenyl)-λ3-iodane (PhIBr2) is proposed as the reactive intermediate. This methodology using PIFA/TMSBr has been applied with success to a great number of substrates (25 examples). The treatment of mono-substituted activated arenes led to para-brominated products (2u-z) in excellent 83-96% yields. Density functional theory calculations indicate a stepwise mechanism involving a double bromine addition followed by a type II dyotropic reaction with concomitant re-aromatization of the six-membered ring.

Stereocontrolled synthesis of C-arylglycosides applied to the south west fragment of the antibiotic kendomycin

A nine step synthesis of the southwest fragment 3 of the antibiotic kendomycin (1) is reported. The tetrahydropyran ring is prepared in a highly stereocontrolled and efficient sequence. The key step concerns an anti-aldol reaction using chiral ketone 10. C-Aryl glycoside 3 exhibits atropisomerism and the relative configuration around its tetrahydropyran ring was established by NOE experiments.

Synthesis of 9a-Deoxymitomycin Congeners

The protected mitosane (23) is prepared in stereospecific manner.The key reactions included in the synthetic scheme are (i) Lewis acid-mediated Claisen-type rearrangement of the penta-2,4-dienyl aryl ether (10) to the penta-2,4-dienylphenol (11), (ii) the regioselective incorporation of the alkoxymethyl group at the 1-position of the pentadienyl side-chain in the protected pentadienylhydroquinone (12), and (iii) the stereospecific copper-catalysed double cyclization of the azido(penta-2,4-dienyl)quinone (15) to the 3H-pyrroloindole-5,8-dione (16) in one step.Subsequent stereospecific introduction of the aziridine ring furnishes the target compound (23).

Lewis Acid Mediated Claisen-Type Rearrangement of Aryl Dienyl Ethers

Rearrangement of aryl pentadienyl ethers in the presence of BF3*OEt2 affords pentadienyl phenols in good yields without formation of the corresponding rearranged products.The mechanism of this rearrangement was studied by deuterium labeling and cross-coupling reactions.The scope and limitations of the rearrangement are discussed.