5022-20-8

Upstream product

• 5022-23-1 5,7-Dihydroxy-8-(2-methylbutanoyl)-4-propyl-2H-chromen-2-one 
• 870-63-3 prenyl bromide 
• 503-60-6 3,3-dimethyl-allyl chloride 
• 98192-68-8 5,7-dihydroxy-8-(2-methylbutyryl)-4-propylcoumarin 
• 5856-79-1 iso-butyl chloroformate 
• 27763-54-8 (S)-2-methylbutanoyl chloride 
• 39652-80-7 (S)-2-methyl-1-(2,4,6-trihydroxyphenyl)butan-1-one 
• 66346-59-6 5,7-dihydroxy-4-propylcoumarin 
• 108-73-6 3,5-dihydroxyphenol 
• 98216-09-2 (S)-(-)-5,7-dihydroxy-8-(2-methylbutyryl)-4-propylcoumarin 
• 125074-06-8 2-methyl-1-(2,4,6-trihydroxyphenyl)-1-butanone 
• 2437-62-9 1-(2,4,6-trihydroxyphenyl)butan-1-one 
• 1565-80-6 (2S)-2-methyl-1-butanol 
• 3249-68-1 ethyl butyroyl acetate 

Downstream Products

• 30390-04-6 mammea B/BB cyclo F 

Relevant academic research and scientific papers

Synthesis of the Mammea Coumarins. Part 4. Stereochemical and Regiochemical Studies, and Synthesis of (-)-Mammea B/BB

Acylation of phloroglucinol with (S)-2-methylbutyryl chloride followed by Pechmann condensation with ethyl 3-oxohexanoate, or acylation of 5,7-dihydroxy-4-propylcoumarin with (S)-2-methylbutyryl chloride gave an 8-(S)-acylcoumarin that was C-alkylated to afford natural (-)-mammea B/BB: the configuration of the 2-methylbutyryl moiety in the natural coumarins was thus demonstrated to be (S)-Surangin B was likewise prepared as a mixture of 1'S, 2''S)- and (1'R, 2''S)-stereoisomers.The crystal structure and conformation of a 6-acylcoumarin that establishes the orientation of other synthetic coumarins is reported.

Synthesis of Mammea Coumarins. Part 1. The Coumarins of the Mammea A, B, and C Series

The naturally-occuring Mammea coumarins of the 4-phenyl-(mammea A), propyl-(mammea B), and 4-pentyl-(mammea C) series have been prepared by Pechmann condensation of an acylphloroglucinol (3-methylbutyryl-, 2-methylbutyryl-, butyryl-, or 2-methylpropionyl-) with the appropriate β-ketoester to give a mixture of 6- and 8-acyl-5,7-dihydroxycoumarins that could be separated.C-Alkylation with 3-methylbut-2-enyl bromide, or 3,7-dimethylocta-2,6-dienyl chloride, in aqueous potassium hydroxide completed the synthesis of the Mammea coumarins having unmodified prenyl or geranyl substituents; oxidative modification of the prenyl group led to the mammea cyclo E and cyclo F coumarins.Some mammea cyclo D (chromeno) coumarins were synthesized by reaction of acylcoumarins with 1,1-dimethoxy-3-methylbutan-3-ol.