381246-83-9

Upstream product

• 640-68-6 D-Val-OH 
• 17407-56-6 (R)-2-Hydroxy-3-methylbutyric acid 
• 381247-11-6 (2R,3S,4R,5S)-1-(tert-Butyl-diphenyl-silanyloxy)-5-[1,3]dithian-2-yl-3-methyl-hexane-2,4-diol 
• 381246-77-1 2,2-dimethylpropionic acid (2S,3R,4R)-4-benzyloxymethoxy-2-(tert-butyldimethylsilanyloxy)-3,5-dimethylhexyl ester 
• 381246-78-2 2,2-dimethylpropionic acid (2S,3R,4R)-2,4-bis(tert-butyldimethylsilanyloxy)-3,5-dimethylhexyl ester 
• 381247-07-0 (2S,3R,4R)-4-Benzyloxymethoxy-2-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-hexanoic acid methyl ester 
• 381247-08-1 (2S,3R,4R)-4-Benzyloxymethoxy-2-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-hexan-1-ol 
• 381247-09-2 (+)-(2S,3R,4R)-2,4-bis(tert-butyldimethylsiloxy)-3,5-dimethylhexan-1-ol 
• 381246-74-8 (2R,3R,4S,5R,6S)-2,6,7-Trihydroxy-4-methoxymethoxy-3,5-dimethyl-heptanoic acid methyl ester 
• 183201-71-0 (2S,3S,4R)-4-benzyloxymethoxy-2-hydroxy-3,5-dimethylhexanoic acid methyl ester 
• 381247-10-5 (2R,3S,4R,5S)-5-[1,3]Dithian-2-yl-3-methyl-hexane-1,2,4-triol 
• 381246-76-0 (3S,4R)-4-benzyloxymethoxy-3,5-dimethylhexanoic acid methyl ester 
• 381246-81-7 (3R,4R,5R)-5-((S)-1-[1,3]dithian-2-yl-ethyl)-3-hydroxy-4-methyldihydro-furan-2-one 
• 381246-75-9 (E)-(4R)-4-benzyloxymethoxy-5-methylhex-2-enoic acid methyl ester 

Relevant academic research and scientific papers

Total synthesis of bafilomycin A1 relying on iterative 1,2-induction in acyclic precursors

The macrolide bafilomycin A1 was synthesized starting from D-valine and D-mannitol as chiral progenitors of propionate units. Acyclic subunits corresponding to different parts of the molecule were constructed based on an iterative 1,2-asymmetric induction protocol as a distinctive feature of the synthesis. The assembly of two segments encompassing the entire carbon framework of the macrolide was achieved by using a Stille coupling. The resulting seco-ester was further manipulated to provide crystalline bafilomycin A1 via a conventional carbodiimide-mediated Keck-type macrolactonization.