220173-95-5

Upstream product

• 90719-27-0 (S)-3-acryloyl-4-benzyloxazolidin-2-one 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 133467-37-5 (4S)-3-[(2S,3S)-3-hydroxy-2-methyl-3-phenylpropanoyl]-4-benzyl-2-oxazolidinone 
• 131685-53-5 (S)-4-benzyl-3-propionyl-2-oxazolidinone 

Downstream Products

• 220173-96-6 (2R,3S)-3-(tert-butyldimethylsilyloxy)-2-methyl-3-phenylpropan-1-ol 
• 1401337-53-8 (2E,4E,7S,8R,9S)-ethyl 9-(tert-butyldimethylsilyloxy)-7-hydroxy-4,8-dimethyl-9-phenylnona-2,4-dienoate 
• 1401338-08-6 (2E,4E,7R,8R,9S)-ethyl 9-(tert-butyldimethylsilyloxy)-7-hydroxy-4,8-dimethyl-9-phenylnona-2,4-dienoate 

Relevant academic research and scientific papers

Total Synthesis of Nannocystin Ax

The total synthesis of nannocystin Ax in an overall yield of 11% with 14 steps as the longest linear sequence is reported. Nannocystin Ax is a cytotoxic 21-membered depsipeptide and was isolated from the myxobacterial genus Nannocystis sp. The synthesis u

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.