160741-81-1

Upstream product

• 120313-28-2 (2S,3R,4S)-2,4-Dihydroxy-3,5-dimethyl-hexanoic acid diethylamide 
• 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 
• 17407-56-6 (R)-2-Hydroxy-3-methylbutyric acid 
• 640-68-6 D-Val-OH 
• 183201-71-0 (2S,3S,4R)-4-benzyloxymethoxy-2-hydroxy-3,5-dimethylhexanoic acid methyl ester 
• 120313-18-0 (R^*,S^*)-4-hydroxy-3,5-dimethyl-2-oxo-N,N-diethylhexanamide 
• 160741-81-1 (3S,4R,5R)-3-Hydroxy-5-isopropyl-4-methyl-dihydro-furan-2-one 
• 85710-97-0 (4R*,5R*)-4,5-dihydro-5-isopropyl-4-methyl-2(3H)-furanone 

Downstream Products

• 106470-99-9 3(R^*)-hydroxy-4(S^*)-methyl-5(R^*)-isopropyltetrahydrofuran-2-one 

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.

Stereocontrolled functionalization in acyclic systems by exploiting internal 1,2-asymmetric induction - Generation of polypropionate and related motifs

Conjugate organocuprate additions to α,β-unsaturated esters that have a γ-ether substituent take place with high anti-selectivity. Potassium ester enolates can react with electrophiles to give the corresponding α-hydroxy α-alkyl, and α-azido esters with an overall anti/syn orientation of three vicinal groups relative to the initial resident chiral center.

Kinetic Aldol Reactions of α-Keto Amides. Synthesis of the β-Methyl Glycosides of (-)-Cladinose and (+)-Mycarose

The first examples of nondehydrative, kinetic aldol condensations of 3-methyl and 3-phenoxy-2-oxo (tertiary) carboxamides are reported.Addition of hydride or methyl Grignard nucleophiles to the aldol products produced diol or monoprotected triol amides with high stereoselectivity in some cases.One of these compounds was elaborated to the methyl glycosides of (-)-cladinose and (+)-mycarose.