188446-29-9

Upstream product

• 69739-34-0 t-butyldimethylsiyl triflate 
• 188446-25-5 methyl (2S,3S)-2-amino-3-(4-(benzyloxy)phenyl)-3-hydroxypropanoate 
• 4397-53-9 p-benzyloxybenzaldehyde 
• 188446-23-3 (2R,5S,αS)-5-[4'-benzyloxy-α-hydroxy]benzyl-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine 

Downstream Products

• 188446-35-7 (S)-2-[(2S,3S)-2-(tert-Butoxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-3-(4-hydroxy-phenyl)-propionylamino]-3-(3-fluoro-4-nitro-phenyl)-propionic acid methyl ester 
• 188446-34-6 (2S,3S)-2-(tert-Butoxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-3-(4-hydroxy-phenyl)-propionic acid pentafluorophenyl ester 
• 188446-32-4 (2S,3S)-3-(4-Benzyloxy-phenyl)-2-(tert-butoxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid 
• 188446-31-3 (2S,3S)-3-(4-Benzyloxy-phenyl)-2-tert-butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid 
• 188446-33-5 (2S,3S)-2-(tert-Butoxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-3-(4-hydroxy-phenyl)-propionic acid 
• 188446-30-2 (2S,3S)-3-(4-Benzyloxy-phenyl)-2-tert-butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid methyl ester 

Relevant academic research and scientific papers

A Synthetic Route to β-Hydroxytyrosine-Derived Tetramic Acids: Total Synthesis of the Fungal Metabolite F-14329

3-Acyltetramic acids derived from β-hydroxytyrosine are synthetically challenging. The first route to this structural motif, based upon a condensation between a Meldrum's acid conjugate bearing the acyl side chain, and a β-hydroxytyrosinate, N-protected by an ortho-nitrobenzyl group is presented. This group enables the Dieckmann cyclization of the resulting N-(β-ketoacyl)amino ester, after which it can be removed photolytically without compromising the delicate 3′-hydroxy group. This strategy was applied to the first total synthesis of the fungal metabolite F-14329 (1).

Synthesis of (9R,12S)- and (9S,12S)-cycloisodityrosine and their N-methyl derivatives

Full details of the synthesis of (9R,12S)- and (9S,12S)-cycloisodityrosine and their N-methyl derivatives are detailed based on an intramolecular nucleophilic aromatic substitution reaction for formation of the key biaryl ether with 14-membered ring macrocyclization. Their comparison with prior samples and the documentation of a facile C9 epimerization within the natural 9S series are described.