16850-91-2

Upstream product

• 117285-88-8 3,4-dihydro-7-methoxy-6-senecioylcoumarin 
• 114032-19-8 6-(3-hydroxy-3-methylbut-1-yn-1-yl)-7-methoxy-2H-chromen-2-one 
• 54102-23-7 6-bromo-7-methoxycoumarin 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 531-59-9 7-methoxycoumarin 
• 93198-68-6 (E)-methyl 2’-hydroxy-4’-methoxycinnamate 
• 144582-47-8 methyl 2'-acetoxy-4'-methoxycinnamate 
• 117285-70-8 methyl 3-(4-methoxy-2-senecioyloxyphenyl)propanoate 
• 117285-76-4 methyl 3-(2-hydroxy-4-methoxy-5-senecioylphenyl)propanoate 
• 69471-28-9 methyl 3-(2'-hydroxy-4'-methoxyphenyl)propanoate 

Downstream Products

• 63975-56-4 hopeyhopin 
• 16850-93-4 (E)-3-(5-Acetyl-2,4-dimethoxy-phenyl)-acrylic acid 

Relevant academic research and scientific papers

Syntheses of 6-acylcoumarins via highly regioselective fries rearrangements. Total syntheses of the linear acylated coumarins geijerin and dehydrogeijerin

Methyl 3-(2-acyloxy-4-methoxyphenyl)propanoates (7), prepared in high yield from 7-methoxycoumarin are key intermediates in general and efficient syntheses of 6-acylcoumarins. Under standard Fries rearrangement conditions (7) undergo highly regioselective

EFFICIENT, HIGHLY REGIOSELECTIVE FRIES REARRANGEMENTS OF METHYL 3-(2-ACYLOXY-4-METHOXYPHENYL)PROPANOATES: THE FIRST TOTAL SYNTHESIS OF THE LINEAR ACYLATED COUMARINS GEIJERIN AND DEHYDROGEIJERIN.

Aluminium chloride catalysed para-Fries rearrangement of methyl 3-(2-acyloxy-4-methoxyphenyl)propanoates (5) in nitromethane furnishes the corresponding 5-acylated products (6) cleanly and in high yield.The rearrangement products may be converted into 6-a

Natural Product Chemistry, 118. - Synthesis of the Coumarins 6- and 8-Naphthoherniarin, Dehydrogeijerin, and Murraol

The Pd/Cu-catalysed reaction of 6-bromo-7-methoxycoumarin (1) with 2-methyl-3-butyn-2-ol yields 1,2-dehydrosuberenol (2).By Lindlar reduction, water elimination, Diels-Alder reaction with 2-methoxy-p-benzoquinone (6), and dehydrogenation with 6-naphthoherniarin (9), a novel coumarin from Ruta graveolens is synthesized.Dehydrogeijerin (8) is available by Schuster-Meyer rearrangement of 2.By Heck vinylation 8-iodo-7-methoxycoumarin (11) is transferred into murraol (12).By water elimination from 12, Diels-Alder reaction with 6 and aromatisation 8-naphthoherniarin (14) is available.