173218-35-4

Upstream product

• 186581-53-3 diazomethane 
• 173327-01-0 C₅₂H₉₄O₁₁Si₃ 
• 870296-61-0 ethyl (1R,2S,3S,4R,5S)-4-[(S)-O-acetylmandeloyloxy]-2-hydroxy-3-(4-methoxybenzyloxy)-5-methyl-2-(2-trimethylsilyl-3-furyl)cyclohexane-1-carboxylate 
• 173289-84-4 ethyl (1R,2S,3R,5S)-3-[(S)-O-(chloroacetyl)mandeloyloxy]-2-hydroxy-5-methyl-2-(2-trimethylsilyl-3-furyl)-4-oxocyclohexane-1-carboxylate 
• 173396-45-7 ethyl (1R,2S,3R,5S)-2,3-dihydroxy-5-methyl-2-(2-trimethylsilyl-3-furyl)-4-oxocyclohexane-1-carboxylate 
• 173289-85-5 ethyl (1R,2S,3R,4S,5R)-2,3-dihydroxy-5-methyl-5-phenylselanyl-4-trichloroacetoxy-2-(2-trimethylsilyl-3-furyl)cyclohexane-1-carboxylate 
• 173289-88-8 2-trimethylsilylethyl (1R,2S,3R,4R)-2-hydroxy-4-methoxy-5-methyl-3-(2-trimethylsilylethoxy)methoxy-2-(2-trimethylsilyl-3-furyl)cyclohex-5-ene-1-carboxylate 
• 870296-74-5 2-trimethylsilylethyl (1R,2S,3R,4R)-2-hydroxy-2-(5-hydroxy-2-oxo-1-oxacyclopent-3-en-3-yl)-4-methoxy-5-methyl-3-(2-trimethylsilylethoxy)methoxycyclohex-5-ene-1-carboxylate 
• 173396-48-0 ethyl (1R,2S,5R)-2-hydroxy-5-methyl-5-phenylselanyl-2-(2-trimethylsilyl-3-furyl)-3,4-dioxocyclohexane-1-carboxylate 
• 173289-89-9 ethyl (1R,2S,3R,4R)-2-hydroxy-4-methoxy-5-methyl-3-(2-trimethylsilylethoxymethoxy)-2-(2-trimethylsilyl-3-furyl)cyclohex-5-ene-1-carboxylate 
• 173396-49-1 ethyl (1R,2S,3R,4S,5R)-5-methyl-5-phenylselanyl-2,3,4-trihydroxy-2-(2-trimethylsilyl-3-furyl)-cyclohexane-1-carboxylate 
• 173289-90-2 (1R,2S,3R,4R)-2-hydroxy-4-methoxy-5-methyl-3-(2-trimethylsilylethoxy)methoxy-2-(2-trimethylsilyl-3-furyl)cyclohex-5-enoic acid 
• 173396-47-9 ethyl (1R,2S)-2,4-dihydroxy-5-methyl-2-(2-trimethylsilyl-3-furyl)-3-oxocyclohex-4-ene-1-carboxylate 
• 173396-52-6 ethyl (1R,2S,3R,4R)-2,3-dihydroxy-4-methoxy-5-methyl-2-(2-trimethylsilyl-3-furyl)cyclohex-5-ene-1-carboxylate 

Downstream Products

• 173218-40-1 (6R)-28-chloro-28-deoxy-6-hydroxymilbemycin E 
• 173218-39-8 (6R)-6-hydroxymilbemycin E 
• 173218-36-5 (1R,2S,3R,4R)-2-[(5R,1Z,3E,7E)-1-carbomethoxy-5,7-dimethyl-9-{(2R,3S,6R,8R,10S)-10-hydroxy-3-methyl-2-(1-methylethyl)-1,7-dioxaspiro[5.5]undecan-8-yl}nona-1,3,7-trien-1-yl]-2,3-dihydroxy-4-methoxy-5-methylcyclohex-5-ene-1-carboxylic acid 

Relevant academic research and scientific papers

A total synthesis of milbemycin G: Approaches to the C(1)-C(10)-fragment and completion of the synthesis

A synthesis of the hydroxybutenolide (-)-6 required for synthesis of α-milbemycins and the completion of a total synthesis of milbemycin G 7 is reported. Following preliminary studies, an optimised synthesis of the hydroxybutenolide (-)-6 from the hydroxy

Total Synthesis of Milbemycin G: Assembly and Completion of the Synthesis

The Wittig reaction between phosphonium salt 1 and the hydroxybutenolide 2 followed by deprotection, macrocyclisation, and reduction gives the 6-hydroxymilbemycin E 9 which by further cyclisation is converted into milbemycin G 11.