26477-64-5

Upstream product

• 111249-63-9 ethyl 3-oxo-4-acetoxyhexanoate 
• 71669-30-2 2-acetoxybutyroyl chloride 
• 111249-87-7 dihydroxy-5,7 (acetoxy-1 propyl)-4 coumarine 
• 108-73-6 3,5-dihydroxyphenol 
• 98498-78-3 4-(1-acetoxypropyl)-5,7-dihydroxy-8-(3-methylbutyryl)coumarin 
• 870-63-3 prenyl bromide 

Relevant academic research and scientific papers

Synthesis of the Mammea Coumarins. Part 3. The Insecticidal Coumarins of the Mammea E Series, Mammea D/BB, and a Dihydrocoumarin of the Mammea C Seies

A dihydrocoumarin metabolite of Mammea africana has been prepared by Lewis acid-mediated acylation of 5,7-dihydroxy-4-pentyl-3,4-dihydrocoumarin (available by hydrogenation of the corresponding coumarin).Acylation of 4-(1-methylpropyl)- and 4-(1-acetoxypropyl)-5,7-dihydroxycoumarin, each prepared by Pechmann condensation of phloroglucinol with the appropriate β-keto ester, gave 8-acylcoumarins that have been C-alkylated with 3-methyl-but-2-enyl bromide to provide, respectively, mammea D/BB (ferruol A), and the natural insecticidal 4-(1-acetoxypropyl) coumarins of M. americana, mammea E/BA and E/BB; C-alkylation with 3,7-dimethylocta-2,6-dienyl chloride of 4-(1-acetoxypropyl)-5,7-dihydroxy-8-(2-methylbutyryl)coumarin afforded surangin B, an insecticidal component of M.Iongifolia.