135352-18-0

Upstream product

• 114047-82-4 ethyl 3-oxo-3-(2'-trimethylsilyl-3'-furyl)propanoate 
• 103791-04-4 Benzyloxymethyl isopropenyl ketone 
• 135352-16-8 ethyl (1RS,2SR,3RS,5SR)-3-benzyloxy-2-hydroxy-5-methyl-2-(2-trimethylsilyl-3-furyl)-4-oxocyclohexane-1-carboxylate 

Downstream Products

• 135352-20-4 ethyl (1RS,2SR,3RS,4RS,5SR)-2-hydroxy-4-methoxy-5-methyl-3-(2-trimethylsilylethoxymethoxy)-2-(2-trimethylsilyl-3-furyl)cyclohexane-1-carboxylate 
• 135352-22-6 2-trimethylsilylethyl (1RS,2SR,3RS,4RS,5SR)-2-hydroxy-2-[5-hydroxy-2-oxo-1-oxacyclopent-3-en-3-yl]-4-methoxy-5-methyl-3-(2-trimethylsilylethoxy)methoxycyclohexane-1-carboxylate 
• 135352-21-5 2-trimethylsilylethyl (1RS,2SR,3RS,4RS,5SR)-2-hydroxy-4-methoxy-5-methyl-3-(2-trimethylsilylethoxy)methoxy-2-(2-trimethylsilyl-3-furyl)cyclohexane-1-carboxylate 
• 135352-19-1 ethyl (1RS,2SR,3RS,4RS,5SR)-2,3-dihydroxy-5-methyl-4-phenylethanoyloxy-2-(2-trimethylsilyl-3-furyl)cyclohexane-1-carboxylate 
• 135352-19-1 ethyl (1RS,2SR,3SR,4RS,5SR)-2,3-dihydroxy-5-methyl-4-phenylethanoyloxy-2-(2-trimethylsilyl-3-furyl)cyclohexane-1-carboxylate 
• 135415-62-2 6β-Hydroxy-3,4-dihydromilbemycin E 

Relevant academic research and scientific papers

Total synthesis of milbemycins: A synthesis of (6R)-6-hydroxy-3,4- dihydromilbemycin E

Following studies using benzyloxymethyl isopropenyl ketone 5 and ethyl 3-(3-furyl)-3-oxopropanoate 6, Robinson reactions between aryloxymethyl isopropenyl ketones 19 and 5 and ethyl 3-(2-trimethylsilyl-3-furyl)-3- oxopropanoate 20 were found to be stereos

Milbemycin synthesis: Synthesis of 6β-hydroxy-3,4-dihydromilbemycin E

The hydroxycyclohexanone (7) is readily available via a Robinson annelation, and is converted into the hydroxybutenolide (15) which is incorporated into a synthesis of 6β-hydroxy-3,4-dihydromilbemycin E (28).