850888-99-2

Upstream product

• 250739-30-1 4-amino-3-(2,2-dimethoxy-ethyl)-phenol 
• 98-59-9 p-toluenesulfonyl chloride 
• 850888-98-1 N-[2-(2,2-dimethoxy-ethyl)-4-hydroxy-phenyl]-4-methyl-benzenesulfonamide 
• 850888-79-8 N-[2-(2,2-dimethoxy-ethyl)-4-oxo-cyclohexa-2,5-dienylidene]-4-methyl-benzenesulfonamide 
• 850888-80-1 C₂₀H₁₇NO₃S 
• 358-23-6 trifluoromethylsulfonic anhydride 

Downstream Products

• 851029-98-6 C₂₄H₂₅NO₄S 
• 107368-93-4 (+/-)-cis-trikentrin B 
• 850888-81-2 C₂₁H₁₈F₃NO₇S₂ 

Relevant academic research and scientific papers

Total synthesis of (±)-herbindole B and (±)-cis-trikentrin B

(Chemical Equation Presented) Herbindole B and cis-trikentrin B are naturally occurring indoles having the unusual and synthetically challenging pattern of carbon substitution at the 4-7 and 5-7 positions, respectively, with no substitution at the 1-3 positions. The total syntheses of these polyalkylated indoles have been achieved in 19 and 12 steps, respectively. The synthesis of herbindole B relies on two iterations of a quinine monoimine Diels-Alder reaction, while cis-trikentrin B uses a single cycloaddition of a suitable quinone monoimine. Indolization of the adducts provides suitably substituted benzopyrrole nuclei for elaboration to the natural products.