174647-71-3

Upstream product

• 174647-65-5 tert-Butyl-{(R)-2-[(3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-1-phenyl-buta-2,3-dienyloxy}-diphenyl-silane 
• 149180-78-9 (R)-2-[(3aR,5R,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-1-phenyl-buta-2,3-dien-1-ol 
• 100-52-7 benzaldehyde 
• 174757-47-2 (1R,2S,3S)-1-(t-butyldiphenylsilyloxy)-3,4-isopropylidenedioxy-1-phenylbutan-2-ol 
• 174647-70-2 (1R,2R,3S)-1-(4-butyldiphenylsilyloxy)-3,4-isopropylidenedioxy-1-phenylbutan-2-ol 
• 174647-74-6 (1R,3R)-1-(t-butyldiphenylsilyloxy)-3,4-isopropylidenendioxy-1-phenylbutan-2-one 
• 174647-67-7 (1R,2R)-1-(t-butyldiphenylsilyloxy)-1-phenylbut-3-en-2-ol 
• 174647-66-6 (R)-4-(t-butyldiphenylsilyloxy)-4-phenylbut-1-en-3-one 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 98-59-9 p-toluenesulfonyl chloride 
• 174757-48-3 (1R,2S,3R)-1-(t-butyldiphenylsilyloxy)-1-phenylbutane-2,3,4-triol 

Downstream Products

• 174757-50-7 (1R,2S,3S)-3,4-epoxy-1-phenylbutane-1,2-diol 

Relevant academic research and scientific papers

Total synthesis of (+)-goniodiol

Cytotoxic styryl lactone, (+)-goniodiol 1, was prepared in enantioenriched form (33 92%) in 15 steps from the α-(α'-alkoxyallenic) alcohol 5.

Enantioselective synthesis of (+)-goniodiol and of its naturally occurring acetylated analogs

A novel route to enantioenriched (+)-goniodiol and its natural acetylated derivatives, potent cytotoxic compounds, is described. The main features of this synthesis are transfer of the asymmetric information of the scalemic allenic alcohol 5 to the α- and β- carbons through highly diastercoselective reactions and introduction of the α,β-unsaturated lactone moiety by the Ghosez' methodology.