104528-83-8

Upstream product

• 64-17-5 ethanol 
• 32161-30-1 (S)-3,4-dimethoxyphenylalanine 
• 23234-41-5 2-Amino-3-(3,4-dihydroxy-phenyl)-propionic acid ethyl ester; hydrochloride 
• 59-92-7 3,4-dihydroxy-L-phenylalanine 
• 128217-61-8 2-tert-Butoxycarbonylamino-3-(3,4-dimethoxy-phenyl)-propionic acid ethyl ester 

Downstream Products

• 128217-65-2 2-Allyloxycarbonylamino-3-(3,4-dimethoxy-phenyl)-propionic acid ethyl ester 
• 128217-76-5 2-Allyloxycarbonylamino-3-(4,5-dimethoxy-2-nitro-phenyl)-propionic acid ethyl ester 
• 372965-64-5 (S)-N-(4-methylpent-3-enyl)-3-(3,4-dimethoxyphenyl)alanine ethyl ester 
• 35149-81-6 N-benzoyl-(S)-3,4-dimethoxyphenylalanine 
• 372965-69-0 (1S,4aS,10aS)-2-benzyl-7-chloro-1-(3,4-dimethoxybenzyl)-1,2,3,4,4a,5,10,10a-octahydro-5,5-dimethylbenzo[b][1,7]naphthyridine 
• 372965-68-9 (1S,4aR,10aS)-2-benzyl-7-chloro-1-(3,4-dimethoxybenzyl)-1,2,3,4,4a,5,10,10a-octahydro-5,5-dimethylbenzo[b][1,7]naphthyridine 
• 372965-65-6 (S)-N-benzyl-N-(4-methylpent-3-enyl)-3-(3,4-dimethoxyphenyl)alanine ethyl ester 
• 372965-71-4 (1S,4aS,10aS)-1-(3,4-dimethoxybenzyl)-1,2,3,4,4a,5,10,10a-octahydro-5,5-dimethylbenzo[b][1,7]naphthyridine 
• 372965-70-3 (1S,4aR,10aS)-1-(3,4-dimethoxybenzyl)-1,2,3,4,4a,5,10,10a-octahydro-5,5-dimethylbenzo[b][1,7]naphthyridine 
• 372965-66-7 (S)-N-benzyl-3-(3,4-dimethoxyphenyl)-N-(4-methylpent-3-enyl)alaninol 
• 372965-67-8 (S)-N-benzyl-3-(3,4-dimethoxyphenyl)-N-(4-methylpent-3-enyl)alaninal 

Relevant academic research and scientific papers

Rh(iii)-Catalyzed diastereoselective transfer hydrogenation: An efficient entry to key intermediates of HIV protease inhibitors

A highly efficient diastereoselective transfer hydrogenation of α-aminoalkyl α′-chloromethyl ketones catalyzed by a tethered rhodium complex was developed and successfully utilized in the synthesis of the key intermediates of HIV protease inhibitors. With the current Rh(iii) catalyst system, a series of chiral 3-amino-1-chloro-2-hydroxy-4-phenylbutanes were produced in excellent yields and diastereoselectivities (up to 99% yield, up to 99?:?1 dr). Both diastereomers of the desired products could be efficiently accessed by using the two enantiomers of the Rh(iii) catalyst.

Pictet-Spengler cyclization vs. Aminal formation: Competing reaction pathways of benzo[b][1,7]naphthyridines controlled by the configuration

Diastereoisomeric benzo[b][1,7]naphthyridines 13a,b were synthesized in nine steps from L-DOPA employing a Lewis acid-catalyzed cyclization of N-(4-methylpent-3-enyl)-a-amino aldehydes as the key step. Under aprotic Pictet-Spengler conditions, compounds 13a,b undergo different reaction pathways depending on the relative configuration. Whereas trans,cis-diastereoisomer 13a yielded the desired Pictet-Spengler cyclization product albeit in very low yield, the corresponding concave-shaped all-cis-diastereoisomer 13b undergoes intramolecular animal formation.

Synthesis of the Chromophore of Pseudobactin, a Fluorescent Siderophore from Pseudomonas

Protected forms of dihydroxyphenylalanine (DOPA) were converted to the corresponding dihydroquinolin-2-ones 13 by nitration and reductive cyclization.Subsequent N-alkylation with α-halo-γ-aminobutyric acid derivatives provided the carbon framework 12 for the chromophore of pseudobactin.Conversion to protected forms of the fluorescent chromophore 5 was accomplished by reaction of 12 with Lawesson's reagent to produce the corresponding thioamide which was cyclized by reaction with mercuric acetate.