135415-62-2

Upstream product

• 135352-19-1 ethyl (1RS,2SR,3SR,4RS,5SR)-2,3-dihydroxy-5-methyl-4-phenylethanoyloxy-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 
• 129245-36-9 (2R,4E)-6-<(2R,4S,6R,8R,9S)-4-tert-Butyldimethylsilyloxy-9-methyl-8-isopropyl-1,7-dioxaspiro<5.5>undecan-2-yl>-2,4-dimethylhex-4-enyl(triphenyl)phosphonium iodide 
• 135352-23-7 C₅₂H₉₆O₁₁Si₃ 
• 135352-24-8 C₄₆H₈₂O₁₀Si₂ 
• 135352-26-0 C₄₅H₇₈O₉Si₂ 
• 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 
• 135352-22-6 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 
• 135352-16-8 ethyl (1RS,2SR,3RS,5SR)-3-benzyloxy-2-hydroxy-5-methyl-2-(2-trimethylsilyl-3-furyl)-4-oxocyclohexane-1-carboxylate 
• 135352-18-0 ethyl (1RS,2SR,3SR,4RS,5SR)-3-benzyloxy-2,4-dihydroxy-5-methyl-2-(2-trimethylsilyl-3-furyl)cyclohexane-1-carboxylate 
• 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 
• 114047-82-4 ethyl 3-oxo-3-(2'-trimethylsilyl-3'-furyl)propanoate 
• 871023-00-6 methyl (6R,2Z,4E,8E)-10-{(2R,3S,6R,8R,10S)-10-tert-butyldimethylsilyloxy-3-methyl-2-(1-methylethyl)-1,7-dioxaspiro[5.5]undecan-8-yl}-2-[1-(2-trimethylsilylethoxycarbonyl)-2,3-dihydroxy-4-methoxy-5-methyl-cyclohexan-2-yl]-6,8-dimethyldeca-2,4,8-trienoate 
• 871023-02-8 3-{8-[4-(tert-butyl-dimethyl-silanyloxy)-8-isopropyl-9-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-4,6-dimethyl-octa-2,6-dienylidene}-3a-hydroxy-7-methoxy-6-methyl-2-oxo-octahydro-benzofuran-4-carboxylic acid 2-trimethylsilanyl-ethyl ester 

Relevant academic research and scientific papers

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).

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