381246-91-9

Upstream product

• 381246-90-8 (4S,5S)-4-benzyloxymethoxy-7-methoxymethoxy-5-methylhept-2-trans-enoic acid methyl ester 
• 139190-55-9 (3S,4S)-4-[(benzyloxy)methoxy]-5-(tert-butyldiphenylsilanyloxy)-3-methylpentanoic acid methyl ester 
• 381247-12-7 ((2S,3S)-2-Benzyloxymethoxy-5-methoxymethoxy-3-methyl-pentyloxy)-tert-butyl-diphenyl-silane 
• 381246-89-5 (2S,3S)-2-benzyloxymethoxy-5-methoxymethoxy-3-methylpentan-1-ol 
• 381247-21-8 (3S,4S)-4-Benzyloxymethoxy-5-(tert-butyl-diphenyl-silanyloxy)-3-methyl-pentan-1-ol 

Downstream Products

• 88899-55-2 bafilomycin A₁ 
• 381247-14-9 (3R,4S,5S)-4-Benzyloxymethoxy-7-methoxymethoxy-3,5-dimethyl-heptane-1,2-diol 
• 381247-13-8 (3R,4S,5S)-4-Benzyloxymethoxy-2-hydroxy-7-methoxymethoxy-3,5-dimethyl-heptanoic 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.