855301-78-9

Upstream product

• 677751-22-3 (1R,3R,4R,6R,7S,8R,12S)-3,7-bis(benzyloxy)-4-(t-butyldimethylsilyloxy)-12-hydroxy-1-hydroxymethyl-6-(4-methoxybenzyloxy)-5,5-dimethyl-9-methylenebicyclo[6.4.0]dodecan-2-one 
• 677751-25-6 (1R,3R,4R,6R,7S,8R,12S)-3,7-bis(benzyloxy)-4-(t-butyldimethylsilyloxy)-12-hydroxy-1-methoxymethoxymethyl-6-(4-methoxybenzyloxy)-5,5-dimethyl-9-methylenebicyclo[6.4.0]dodecan-2-one 

Downstream Products

• 815598-50-6 (1R,2S,3S,4R,6R,7S,8R,12S)-3,7-bis(benzyloxy)-4-(t-butyldimethylsilyloxy)-2,12-(isopropylidenedioxy)-6-(4-methoxybenzyloxy)-1-(methoxymethoxymethyl)-5,5-dimethyl-9-methylenebicyclo[6.4.0]dodecane 
• 815598-49-3 (4S,4aR,5S,6S,7R,8R,11S,12S,12aR)-6,12-bis(benzyloxy)-11-(cyclohexyldimethylsilyloxy)-4,5-(isopropylidenedioxy)-4a-(methoxymethoxymethyl)-8,13,13-trimethyl-1-methylenetetradecahydro-7,11-methanobenzocyclododecene-7,8-dilo 
• 815598-54-0 (1R,2S,3S,4R,6S,7S,8R,12S)-3,7-bis(benzyloxy)-6-(3-butenyl)-6-(cyclohexyldimethylsilylenedioxy)-2,12-(isopropylidenedioxy)-1-(methoxymethoxymethyl)-5,5-dimethyl-9-methylenebicyclo[6.4.0]dodecane 
• 855301-80-3 (1R,2S,3S,4R,6S,7S,8R,12S)-3,7-bis(benzyloxy)-6-(3-butenyl)-6-(cyclohexyldimethylsilylenedioxy)-2,12-(isopropylidenedioxy)-1-(methoxymethoxymethyl)-5,5-dimethyl-9-methylenebicyclo[6.4.0]dodecan-4-one 
• 815598-55-1 (1R,2S,3S,6S,7S,8R,12S)-3,7-bis(benzyloxy)-6-(cyclohexyldimethylsilyloxy)-2,12-(isopropylidenedioxy)-1-(methoxymethoxymethyl)-5,5-dimethyl-9-methylene-6-(3-oxobutyl)bicyclo[6.4.0]dodecan-4-one 
• 815598-53-9 (1R,2S,3S,4R,6S,7S,8R,12S)-3,7-bis(benzyloxy)-6-(3-butenyl)-4,6-(cyclohexylmethylsilylenedioxy)-2,12-(isopropylidenedioxy)-1-(methoxymethoxymethyl)-5,5-dimethyl-9-methylenebicyclo[6.4.0]dodecane 
• 815598-52-8 (1R,2S,3S,5R,6S,7S,8R,9S)-2,6-bis(benzyloxy)-3-(3-butenyl)-5-(t-butyldimethylsilyloxy)-7,9-(isopropylidenedioxy)-8-(methoxymethoxymethyl)-4,4-dimethyl-12-methylenebicyclo[6.4.0]dodecan-3-ol 
• 855301-76-7 (1S,4aR,5S,6S,9R,10R,11S,12S,12aR)-6-(cyclohexyldimethylsilyloxy)-1,12-(isopropylidenedioxy)-12a-(methoxymethoxymethyl)-9,13,13-trimethyl-4-methylenetetradecahydro-6,10-methanobenzocyclodecene-5,9,10,11-tetrol 
• 815598-62-0 (1R,2S,3S,5R,6S,7S,8R,9S)-2,6-bis(benzyloxy)-5-(t-butyldimethylsilyloxy)-7,9-(isopropylidenedioxy)-8-(methoxymethoxymethyl)-4,4-dimethyl-12-methylenebicyclo[6.4.0]dodecan-3-ol 
• 855301-65-4 (1R,2S,3S,5R,6S,7S,8R,9S)-2,6-bis(benzyloxy)-3-(3-butenyl)-5-(t-butyldimethylsilyloxy)-7,9-(isopropylidenedioxy)-8-(methoxymethoxymethyl)-4,4-dimethyl-12-methylenebicyclo[6.4.0]dodecan-3-ol 
• 815598-51-7 (1R,2S,5R,6S,7S,8R,9S)-2,6-bis(benzyloxy)-5-(t-butyldimethylsilyloxy)-7,9-(isopropylidenedioxy)-8-(methoxymethoxymethyl)-4,4-dimethyl-12-methylenebicyclo[6.4.0]dodecan-3-one 

Relevant academic research and scientific papers

Stereoselective synthesis of 19-hydroxytaxoid by utilizing samarium(II) iodide-mediated double aldol cyclization

The stereoselective synthesis of new 19-hydroxytaxoid 36, possessing a double-aldol skeleton was achieved by way of B to BC to ABC ring construction. Optically active 8-membered ring 6 corresponding to the B-ring of 19-hydroxytaxol has been synthesized in high yield from epoxyketo aldehyde 8 by intramolecular samarium(II) iodide-mediated double aldol cyclization. The bicyclic compound 5 corresponding to the BC ring system was prepared from the 8-membered ring 6 by successive trimethylaluminium-assisted stereoselective conjugated addition and intramolecular samarium(II) iodide-mediated double aldol cyclization. The ABC-ring system 4 was constructed by stereoselective homoallylation and pinacol coupling cyclization with low-valent titanium. The synthesis of new 19-hydroxytaxoid 36 was accomplished from ABC ring system 4 by olefination of vicinal diol unit.

Stereoselective synthesis of 19-hydroxytaxoid using intramolecular pinacol coupling reaction

The ABC-ring system of 19-hydroxytaxol is stereoselectively constructed by intramolecular pinacol coupling of diketone 12 with low valent titanium species prepared from TiCl2 and LiAlH4. After manipulations of hydroxy protecting grou