239089-33-9

Upstream product

• 994-30-9 triethylsilyl chloride 
• 51335-75-2 2,2-Dimethyl-1,3-dioxacyclohexane-5,5-dicarboxylic acid,diethyl ester 
• 239089-40-8 (1'R,3'R)-5-{1',3'-Dihydroxy-3'-[furan-2''(5''H)-on-4''-yl]propyl}-5-p-methoxybenzyloxymethyl-2,2-dimethyl-1,3-dioxane 
• 239089-25-9 5,5-Bis(p-methoxybenzyloxymethyl)-2,2-dimethyl-1,3-dioxane 
• 239089-29-3 (1'R)-5-(1'-Hydroxybut-3'-enyl)-5-p-methoxybenzyloxymethyl-2,2-dimethyl-5-(1'-trimethylsilyloxybut-3'-enyl)-1,3-dioxane 
• 239089-26-0 (5-(((4-methoxybenzyl)oxy)methyl)-2,2-dimethyl-1,3-dioxan-5-yl)methanol 
• 239089-27-1 9-(4-methoxyphenyl)-3,3-dimethyl-2,4,8,10-tetraoxaspiro[5.5]undecane 
• 239089-28-2 5-Formyl-5-p-methoxybenzyloxymethyl-2,2-dimethyl-1,3-dioxane 
• 20605-01-0 diethyl bis(hydroxymethyl)malonate 
• 770-74-1 2,2-dimethyl-5,5-bis(hydroxymethyl)-1,3-dioxane 
• 239089-32-8 (1'R,3'S)-5-{1',3'-Dihydroxy-3'-[furan-2''(5''H)-on-4''-yl]propyl}-5-p-methoxybenzyloxymethyl-2,2-dimethyl-1,3-dioxane 

Relevant academic research and scientific papers

Synthetic studies on azadirachtin: An efficient asymmetric synthesis of the highly functionalized tricyclic decalin part of azadirachtin

The detailed examination of intramolecular Diels-Alder reactions of several structurally related trienes led to construction of the desired tricyclic decalin moiety of azadirachtin with the α-hydroxyl groups at C1 and C3 as well as the oxygenated substituent at C8 in the naturally occurring form in good yields.

Synthetic studies on azadirachtin: Construction of the highly functionalized decalin moiety of azadirachtin

Construction of the left segment of azadirachtin in naturally occurring enantiomer is described. The key reaction is an intramolecular Diels-Alder reaction, which was performed under thermal conditions to afford the highly functionalized decalin compounds selectively.