1401338-39-3

Upstream product

• 104410-90-4 tert-butyldimethylsilyl trifluoroacetate 
• 376585-98-7 (S)-9-benzyl-3-[(2S,3S)-5-(tert-butyldimethylsilyl)-3-hydroxy-2-methylpent-4-ynoyl]oxazolidin-2-one 
• 86318-61-8 (tert-butyldimethylsilyl)acetylene 
• 90083-19-5 3-(tert-butyldimethylsilyl)-2-propynal 
• 69739-34-0 t-butyldimethylsiyl triflate 

Downstream Products

• 1401338-56-4 C₂₆H₄₆O₃Si₂ 
• 1401338-57-5 C₁₄H₁₈O₃ 
• 1401338-58-6 C₂₀H₃₂O₃Si 

Relevant academic research and scientific papers

Total synthesis of the antibiotic Elansolid B1

The antibiotic elansolid B1 was prepared by a convergent strategy that relied on a highly diastereoselective, biomimetic intramolecular Diels-Alder cycloaddition (IMDA) that furnished the tetrahydroindane unit. Other key features are a double Sonogashira cross-coupling and a substratecontrolled Yamamoto aldol reaction.

Substrate-controlled stereoselectivity in the Yamamoto aldol reaction

The Yamamoto aldol reaction is a vinylogous aldol reaction that relies on bulky aluminium-based Lewis acids. These activate both the aldehyde as well as become part of the enolate moiety. The report discloses the first detailed study on the substrate-controlled Yamamoto aldol reaction in which 2,3-syn and 2,3-anti disubstituted aldehydes serve as the stereodirecting elements. The "size" of the substituent in the β-position strongly determines the facial selectivity of enolate addition to the aldehyde. Large substituents favour formation of 1,3-syn diols while slim alkynyl groups preferentially lead to 1,3-anti products. The Royal Society of Chemistry 2012.