126357-82-2

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 5673-07-4 2,6-dimethoxytoluene 
• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 69739-34-0 t-butyldimethylsiyl triflate 

Downstream Products

• 887601-14-1 [2-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-phenyl]-(1,4-dioxa-spiro[4.5]dec-7-en-8-yl)-methanol 
• 947232-31-7 tert-butyl(2-(2,2-dibromovinyl)-6-methoxyphenoxy)-dimethylsilane 
• 1170695-42-7 C₂₇H₃₈O₅Si 
• 1228645-66-6 1-[2-(tert-butyldimethylsilyloxy)-3-methoxyphenyl]prop-2-en-1-ol 
• 1606589-75-6 (4a′S,5′S,8a′S)-5′-[2-(tert-butyldimethylsiloxy)-3-methoxybenzyl]-5′,8a′-dimethylhexahydro-2′Hspiro{[1,3]dioxolane-2,1′-naphthalen}-6′(7′H)-one 
• 1628714-20-4 2-(1-(3,4-dimethoxyphenyl)but-3-enyl)-6-methoxyphenol 
• 1628714-21-5 (E)-2-(1-(3,4-dimethoxyphenyl)but-2-enyl)-6-methoxyphenol 
• 1628714-22-6 (Z)-2-(1-(3,4-dimethoxyphenyl)but-2-enyl)-6-methoxyphenol 
• 121311-34-0 2-[(3,4-dimethoxyphenyl)(hydroxy)methyl]-6-methoxyphenol 
• 1628714-19-1 (2-(tert-butyldimethylsilyloxy)-3-methoxyphenyl)(3,4-dimethoxyphenyl)methanol 

Relevant academic research and scientific papers

Total Synthesis of (S)-Cularine via Nucleophilic Substitution on a Catechol

Catechols are part of many essential chemicals and are valuable, typically nucleophilic intermediates used in synthesis. Here we describe an unexpected transformation in which they play the role of the electrophile in a formal nucleophilic aromatic substitution. We made this discovery while studying a seven-membered dioxepin ring formation during a synthesis of the benzyltetrahydroisoquinoline (S)-cularine. We suggest a chain mechanism for this new transformation that is triggered by molecular oxygen and that propagates an electrophilic ortho-quinone.

Synthesis of Racemic, Diastereopure, and Enantiopure Carba- or Oxa[5]-, [6]-, [7]-, and -[19]helicene (Di)thiol Derivatives

A series of carba- or oxa[5]-, [6]-, [7]-, and -[19]helicene (di)thiols was prepared. The Miyazaki-Newman-Kwart rearrangement of (dimethylcarbamothioyl)oxy (oxa)helicenes in a flow reactor or nucleophilic substitution of dichloro (oxa)helicenes with alkan

BENZOSUBERENE ANALOGUES AND RELATED COMPOUNDS WITH ACTIVITY AS ANTICANCER AGENTS

A series of benzosuberene analogues demonstrate effective inhibition of tubulin polymerization, cytotoxicity against human cancer cell lines, and vascular disruption in tumors.

Enantioselective Construction of Spiro[chroman-thiazolones]: Bifunctional Phosphonium Salt-Catalyzed [2+4] Annulation between 5-Alkenyl Thiazolones and ortho-Hydroxyphenyl-Substituted para-Quinone Methides

The enantioselective formal [2+4] annulation of 5-alkenyl thiazolones with hydroxyl-substituted para-quinone methides was disclosed by dipeptide-based phosphonium salt catalysts. A wide range of functionalized spiro-chroman-thiazolone molecules bearing three contiguous 3° and/or 4° stereocenters were readily constructed in high yields with excellent stereoselectivities (>20:1 dr and up to >99.9% ee) under low catalyst loading and mild reaction conditions. The practicality and utility of this protocol were demonstrated by the scaled-up preparation and elaborations of product. (Figure presented.).

Structure Guided Design, Synthesis, and Biological Evaluation of Novel Benzosuberene Analogues as Inhibitors of Tubulin Polymerization

A promising design paradigm for small-molecule inhibitors of tubulin polymerization that bind to the colchicine site draws structural inspiration from the natural products colchicine and combretastatin A-4 (CA4). Our previous studies with benzocycloalkeny

Bifunctional Phosphonium Salt Directed Enantioselective Formal [4 + 1] Annulation of Hydroxyl-Substituted para-Quinone Methides with α-Halogenated Ketones

A highly diastereo- and enantioselective [4 + 1] cycloaddition of para-quinone methides to α-halogenated ketones was realized by bifunctional phosphonium salt catalysis, furnishing functionalized 2,3-dihydrobenzofurans in high yields and excellent stereoselectivities (>20:1 dr and up to >99.9% ee). Mechanistic observations suggested that the reaction underwent a cascade intermolecular substitution/intramolecular 1,6-addition process. DFT calculations revealed the presence of multiple H-bonding interactions between the catalyst and the enolate intermediate in the stereodetermining transition states.

(EtO)3SiH-promoted palladium-catalyzed isomerization of olefins: Convenient synthesis of internal alkenes from terminal alkenes

The catalytic activity of an in situ forming palladium catalyst system generated from PdCl2(PPh3)2 and hydrosilane [(EtO)3SiH] was revealed in the one-carbon migration and isomerization of 4,4-biaryl-substituted 1-butenes, in which the (EtO) 3SiH plays a key role in the palladium-catalyzed one-carbon migration and subsequent isomerization of terminal alkenes. This catalytic protocol is applied in the synthesis of a key building block of cassumunin C in high yield and promising selectivity. Georg Thieme Verlag Stuttgart. New York.

Enantioselective total synthesis of dysidavarone A, a novel sesquiterpenoid quinone from the marine sponge dysidea avara

Dysidavaronea A, a structurally unprecedented sesquiterpenoid quinone, was synthesized in 30 % overall yield in a longest liner sequence of 13 steps from commercially available o-vanillin. A highly strained and bridged eight-membered carbocyclic core was established by the C7-C21 carbon bond formation through a copper enolate mediated Michael addition to the internal quinone ring. The power of a copper enolate! Dysidavaronea A, a structurally unprecedented sesquiterpenoid quinone, was synthesized in 30 % overall yield in a longest linear sequence of 13 steps from commercially available o-vanillin (see scheme; TBS=tert-butyldimethylsilyl). A highly strained and bridged eight-membered carbocyclic core was established by the C7-C21 carbon bond formation through a copper enolate mediated Michael addition to the internal quinone ring. Copyright

Regioselective synthesis of phenanthrenes and evaluation of their anti-oxidant based anti-inflammatory potential

Regioselective synthesis of 9,10-Dihydro-2,5-Dimethoxyphenanthrene-1,7-diol (1) and 9,10-Dihydro-2,7-Dimethoxyphenanthrene-1,5-diol (2) was achieved using regioselective methylation, Wittig reaction, intramolecular cyclization and hydrogenation as key ste

Enantioselective copper-catalyzed intramolecular phenolic O-H bond insertion: Synthesis of chiral 2-carboxy dihydrobenzofurans, dihydrobenzopyrans, and tetrahydrobenzooxepines

Efficient: A copper-catalyzed enantioselective intramolecular insertion of carbenoids into phenolic O-H bonds has been developed. This method can be used for the synthesis of the title compounds in high yields and excellent enantioselectivities under mild and neutral conditions (see scheme). NaBAr F=sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate. Copyright