185698-54-8

Upstream product

• 53560-33-1 3,4,5-trimethoxyphenylacetylene 
• 177329-71-4 5-Bromo-1-(tert-butyldimethylsilyloxy)-2-methoxybenzene 
• 203448-30-0 (3-((tert-butyldimethylsilyl)oxy)-4-methoxyphenyl)(3,4,5-trimethoxyphenyl)methanone 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 203448-32-2 phenstatin 
• 90-05-1 2-methoxy-phenol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 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 
• 25016-01-7 5-bromo-2-methoxybenzaldehyde 
• 37942-01-1 5-bromo-2-methoxyphenol 
• 2675-79-8 1-bromo-3,4,5-trimethoxybenzene 

Downstream Products

• 95041-90-0 erianin 
• 117048-62-1 combrestatin A₄ 
• 185698-55-9 2-(3-hydroxy-4-methoxyphenyl)-1-(3',4',5'-trimethoxyphenyl)ethyne 
• 121042-95-3 (Z)-5-(3-tert-butyldimethylsilyloxy-4-methoxystyryl)-1,2,3-trimethoxybenzene 

Relevant academic research and scientific papers

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.

Ethynylation of aryl halides by a modified Suzuki reaction: Application to the syntheses of combretastatin A-4, A-5 and lunularic acid

On treatment with trimethyl borate sodium acetylide undergoes a palladium-catalyzed cross coupling with functionalized aryl halides or triflates in reasonable to good yields. The ethynylarenes thus obtained serve as building blocks for the formation of the highly effective tubulin polymerization inhibitors combretastatin A-4 (1) and A-5 (2) as well as for the synthesis of the plant-growth regulator lunularic acid (36). VCH Verlagsgesellschaft mbH, 1996.