307492-89-3

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 1239588-29-4 C₂₃H₂₈O₄S 
• 307492-87-1 (2S)-(+)-4-bromo-2-methyl-6-tosyloxy-2-tosyloxymethyl-2H-chromene 
• 307492-90-6 C₂₅H₂₅BrO₇S₂ 
• 307492-86-0 C₂₅H₂₆O₇S₂ 
• 307492-81-5 (S)-(+)-2-[2-(2,2,4-trimethyl-1,3-dioxolan-4-yl)ethyl]-4-methoxy-1-(methoxymethox)ybenzene 
• 307492-80-4 (3S)-(+)-2-(3,4-dihydroxy-2,3-epoxy-3-methylbutyl)-4-methoxy-1-methoxymethoxybenzene 
• 307492-79-1 (2R,3R)-2-(2,3-epoxy-4-hydroxy-3-methylbutyl)-4-methoxy-1-methoxymethoxybenzene 
• 434928-87-7 (E)-2-(4-hydroxy-3-methylbut-3-en-1-yl)-4-methoxy-1-methoxymethoxybenzene 
• 307492-85-9 (2S)-(+)-2-hydroxymethyl-2-methylchroman-6-ol 
• 307492-77-9 4-methoxy-1-(methoxymethoxy)-2-(3-methylbut-2-en-1-yl)benzene 
• 150-76-5 4-methoxy-phenol 
• 25458-46-2 4-methoxyphenyl methoxymethyl ether 
• 870-63-3 prenyl bromide 

Relevant academic research and scientific papers

Enantioselective 6-endo-trig Wacker-type cyclization of 2-geranylphenols: Application to a facile synthesis of (-)-cordiachromene

An enantioselective intramolecular oxidative cyclization of 2-geranylphenols catalyzed by a Pd(II)-spiro bis(isoxazoline) complex is reported. The reaction proceeds in a 6-endo-trig manner to give chromene derivatives in reasonable yields and with moderate enantioselectivities. This transformation can be applied to a protecting-group-free total synthesis of naturally occurring cordiachromene.

Enantioselective synthesis of cordiachromene

An enantioselective synthesis of cordiachromene is described. An allylic alcohol moiety is first attached in the o-position to the methoxymethoxy substituent in 1-methoxy-4-methoxymethoxybenzene. Then chirality is introduced successively through asymmetric Sharpless epoxidation on the allylic alcohol moiety and regioselective ring-opening. The chiral diol prepared is then cyclized to chromanmethanol with total retention of configuration. Chromenemethanol is obtained after bromination and dehydrobromination. The total synthesis is achieved by reaction between the tosylated chromene chiral moiety and an organomagnesium prenylated compound.