381247-07-0

Upstream product

• 69739-34-0 t-butyldimethylsiyl triflate 
• 183201-71-0 (2S,3S,4R)-4-benzyloxymethoxy-2-hydroxy-3,5-dimethylhexanoic acid methyl ester 
• 640-68-6 D-Val-OH 
• 17407-56-6 (R)-2-Hydroxy-3-methylbutyric acid 
• 381246-76-0 (3S,4R)-4-benzyloxymethoxy-3,5-dimethylhexanoic acid methyl ester 
• 381246-75-9 (E)-(4R)-4-benzyloxymethoxy-5-methylhex-2-enoic acid methyl ester 
• 381247-06-9 (R)-2-Benzyloxymethoxy-3-methyl-butan-1-ol 
• 381247-05-8 (R)-2-Benzyloxymethoxy-3-methyl-butyric acid methyl ester 
• 906534-74-5 (R)-2-Benzyloxymethoxy-3-methyl-butyraldehyde 
• 90244-32-9 (R)-methyl 2-hydroxy-3-methylbutanoate 

Downstream Products

• 381247-08-1 (2S,3R,4R)-4-Benzyloxymethoxy-2-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-hexan-1-ol 
• 381246-77-1 2,2-dimethylpropionic acid (2S,3R,4R)-4-benzyloxymethoxy-2-(tert-butyldimethylsilanyloxy)-3,5-dimethylhexyl ester 
• 381246-83-9 (4R,5S,6R)-4-((S)-1-{2-[(2R,3S,4R)-2,4-bis(tert-butyldimethylsilanyloxy)-3,5-dimethylhexyl]-[1,3]dithian-2-yl}-ethyl)-6-(tert-butyldiphenylsilanyloxymethyl)-2,2,5-trimethyl-[1,3]dioxane 

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.