925231-63-6

Upstream product

• 1446318-82-6 (4R,5R)-2,2-dimethyl-5-((E)-2-(tributylstannyl)vinyl)-1,3-dioxolan-4-ylmethanol 
• 1446318-81-5 C₂₆H₅₄O₃SiSn 
• 319924-30-6 5-[(tert-Butyldimethylsilyl)oxy]-1,2-dideoxy-3,4-O-(1-methylethylidene)-D-threo-pent-1-yne 
• 125993-65-9 (4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde 
• 73346-74-4 (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol 
• 145554-06-9 [(4R,5R)-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol 
• 194610-23-6 (R)-tert-butyl((4,4-dibromo-2-methylbut-3-en-1-yl)oxy)diphenylsilane 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 95514-03-7 (S)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propionic acid methyl ester 
• 95514-04-8 (R)-3-(tert-butyldiphenylsilyloxy)-2-methylpropan-1-ol 
• 92817-88-4 (2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal 
• 925231-61-4 4-(tert-butyl-dimethyl-silanyloxymethyl)-5-[6-(tert-butyl-diphenyl-silanyloxy)-5-methyl-hexa-1,3-dienyl]-2,2-dimethyl-[1,3]dioxolane 
• 925231-60-3 C₂₁H₂₉BO₃Si 
• 925231-62-5 ((4R,5R)-5-((R,1E,3E)-6-(tert-butyldiphenylsilyloxy)-5-methylhexa-1,3-dienyl)-2,2-dinethyl-1,3-dioxolan-4-yl)methanol 

Downstream Products

• 1446318-83-7 tert-butyl ((R,3E,5E)-6-((4R,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-2-methylhexa-3,5-dienyloxy)diphenylsilane 

Relevant academic research and scientific papers

Formal Total Synthesis of Amphidinolide e

A formal total synthesis of the cytotoxic macrolide amphidinolide E is reported. The strategic steps are three Julia-Kocienski reactions (J-K), for the formation of the C5-C6, C9-C10, and C17-C18 double bonds, a Suzuki-Molander C21-C22 bond formation reaction, and a Kita-Trost macrolactonization. The "instability" of the two dienic systems and of the stereocenter at C2 (allylic methine, α to the carboxy group) and the protecting groups at C17-OH and C18-OH have posed difficult challenges. Each Julia-Kocienski olefination has been systematically optimized to provide the highest possible E/Z ratios.

Synthesis of key fragments of 19-membered cytotoxic macrolide amphidinolide e

Amphidinolide E is a 19-membered macrolide possessing potent cytoxic activity. The macrolide core having two key intermediates alcohol and acid was synthesized efficiently. The THF ring segment was synthesized from Dglucose as chiral precursor, whereas th

Total synthesis of (-)-amphidinolide E

The unique structural features of the cytotoxic marine macrolide (-)-amphidinolide E make it an intriguing synthetic target. Its total synthesis has now been completed by employing a radical cyclization of a β-alkoxy acrylate to form the oxolane ring, a Kocienski-Julia olefination to create the E C=C bond, and a lactonization reaction to close the macrocyclic ring. (Chemical Equation Presented).