185698-55-9

Upstream product

• 185698-54-8 2-[3-(tert-butyldimethylsilyloxy)-4-methoxyphenyl]-1-(3,4,5-trimethoxyphenyl)ethyne 
• 53560-33-1 3,4,5-trimethoxyphenylacetylene 
• 160257-85-2 5-iodo-2-methoxyphenol 
• 25245-29-8 5-iodo-1,2,3-trimethoxybenzene 
• 37942-01-1 5-bromo-2-methoxyphenol 
• 203448-30-0 (3-((tert-butyldimethylsilyl)oxy)-4-methoxyphenyl)(3,4,5-trimethoxyphenyl)methanone 
• 203448-32-2 phenstatin 
• 90-05-1 2-methoxy-phenol 
• 30287-15-1 2-methoxyphenyl 2-chloroacetate 
• 874812-62-1 2-methoxy-5-(3,4,5-trimethoxybenzoyl)phenyl 2-chloroacetate 
• 143287-98-3 3,4,5-trimethoxyphenyl trifluoromethanesulfonate 
• 177329-71-4 5-Bromo-1-(tert-butyldimethylsilyloxy)-2-methoxybenzene 
• 25016-01-7 5-bromo-2-methoxybenzaldehyde 
• 2675-79-8 1-bromo-3,4,5-trimethoxybenzene 

Downstream Products

• 117048-62-1 combrestatin A₄ 
• 95041-90-0 erianin 
• 1042149-59-6 C₂₀H₂₀O₆ 
• 203448-32-2 phenstatin 
• 1580435-99-9 1-(3-hydroxy-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-ortho-carborane 
• 1580436-07-2 1-(4-(benzyloxybenzoyl)phenyl)-2-(3,4,5-trimethoxyphenyl)-ortho-carborane 
• 117048-59-6 trans-combretastatin A-4 
• 852990-46-6 1-(3-hydroxy-4-methoxy-phenyl)-2-(3,4,5-trimethoxy-phenyl)-ethane-1,2-dione 

Relevant academic research and scientific papers

Heterobimetallic Pd/Mn and Pd/Co complexes as efficient and stereoselective catalysts for sequential Cu-free Sonogashira coupling–alkyne semi-hydrogenation reactions

A series of heterobimetallic PdII/MII complexes (MII = Mn, Co) were synthesised and tested as precatalysts for sequential Sonogashira coupling–alkyne semi-hydrogenation reactions to form Z-aryl alkenes. The carbometalated heterobimetallic PdII/CoII complex CoPdL3′ demonstrated an apparent cooperative effect compared to the corresponding monometallic counterparts. This compound was identified as a potent single-molecule catalyst for the one-pot Cu-free Sonogashira coupling of aryl bromides with terminal alkynes followed by chemo- and stereoselective semi-hydrogenation of the alkyne intermediate using NH3·BH3 as a hydrogen source. Furthermore, different aromatic substrates have been tested to show the generality of the reaction for the synthesis of Z-alkenes, including biologically active combretastatin A-4. In addition, the homogeneous nature of the catalytically active species was demonstrated.

Acid-Promoted Intramolecular Decarbonylative Coupling Reactions of Unstrained Ketones: A Modular Approach to Synthesis of Acridines and Diaryl Ketones

Herein, we reported Lewis acid-or Br?nsted acid-promoted intramolecular C(sp2)-C(sp2) bond cleavage and a novel C(sp2)-C(sp2) bond-forming cascade reaction to synthesize the acridine motif. The metal-free oxidation of the alkyne motif generated the in situ ketone group extracted via a decarbonylation reaction. The mechanistic studies revealed that the electrophilic N-iodo species triggered key decarbonylation reactions via consecutive dearomatization/aromatization reactions. In addition, we exploited this acid-promoted C-C bond activation system with internal alkynes to synthesize bis(heteroaryl) ketones.

Diboron-Assisted Copper-Catalyzed Z-Selective Semihydrogenation of Alkynes Using Ethanol as a Hydrogen Donor

We herein describe a B2Pin2-assisted copper-catalyzed semihydrogenation of alkynes. A variety of alkenes were obtained in good to excellent yields with Z-selectivity under mild reaction conditions. Mechanistic studies indicated that a transfer hydrogenation process was involved and ethanol acted as both a solvent and a hydrogen donor in this reaction. The present protocol enabled convenient synthesis of deuterium-substituted Z-alkenes such as Z-Combretastain A4-d2 in a high deuteration ratio by using readily available ethanol-d1 as the deuterium source.

Copper-catalysed, diboron-mediated: Cis -dideuterated semihydrogenation of alkynes with heavy water

Methods to incorporate deuterium atoms into organic molecules are valuable for the pharmaceutical industry. Here, we found that diboron reagents can efficiently mediate the transfer of two D atoms from heavy water directly onto alkynes through copper-catalysed cis-selective semihydrogenation. Avoiding the use of costly and flammable D2 gas, this safe and practical process can proceed with excellent chemoselectivity and stereoselectivity. Utilizing the present method as the key step, the formal asymmetric total synthesis of d2-deuterium-labeled cis-combretastatin A4 is demonstrated. Mechanistic studies suggest that monoborylation of alkynes is the key step for this semihydrogenation process.

cis-Semihydrogenation of alkynes with amine borane complexes catalyzed by gold nanoparticles under mild conditions

Supported gold nanoparticles catalyze the semihydrogenation of alkynes to alkenes with ammonia borane or amine borane complexes in excellent yields and under mild conditions. Internal alkynes provide cis-alkenes, making this protocol an attractive alternative of the classical Lindlar's hydrogenation.

Copper-catalyzed Z-selective semihydrogenation of alkynes with hydrosilane: A convenient approach to cis-alkenes

A copper catalyst generated in situ from widely available copper salt and imidazolium salt in the presence of t-BuOK showed high efficiency for the semihydrogenation of a wide range of internal and terminal alkynes to their corresponding alkenes without obvious over-reduction. Functional groups, such as hydroxyl, nitro, halides, and amino, etc. were tolerated. The Z/E ratios of the obtained alkenes were generally >99%. Finally, semireduction of bulky alkynes also went smoothly.

Diaryl-substituted ortho-carboranes as a new class of hypoxia inducible factor-1α inhibitors

Diaryl-substituted ortho-carboranes 1 were synthesized from the corresponding alkynes by decaborane coupling under microwave-irradiated conditions with a combination of N,N-dimethylaniline and chlorobenzene. Among the compounds synthesized, 1a and 1d exhibited significant inhibition of hypoxia-induced HIF-1 transcriptional activity. Both compounds similarly suppressed hypoxia-induced HIF-1α accumulation in a concentration- dependent manner without affecting HIF-1α mRNA expression.

New efficient synthesis of combretastatin A-4 via Colvin rearrangement

A new four-step approach for the synthesis of anticancer agent combretastatin A-4 (CA-4) has been developed. The method includes the Colvin rearrangement of the benzophenone derivative phenstatin to the key diarylalkyne followed by stereoselective semi-reduction to CA-4 in good overall yield.

Synthesis and antitumor-evaluation of cyclopropyl-containing combretastatin analogs

Several derivatives of combretastatin have been prepared bearing a cyclopropyl unit instead of the natural occurring cis-double bond. Final products and synthetic intermediates were evaluated for their cytotoxic properties in two human cancer cell lines.

A new synthesis of combretastatins A-4 and AVE-8062A

Combretastatins A-4 and AVE-8062A have been synthesized by coupling 3,4,5-trimethoxyphenylacetylene with the corresponding iodomethoxyphenol and bromomethoxyaniline, followed by hydrolysis of the thermally-stable Ti(II)-alkyne complexes.