500548-75-4

Upstream product

• 90878-19-6 phenethylmagnesium chloride 
• 500548-54-9 tert-butyl (2S)-5-bromo-2-(methoxyacetyl)indoline-1-carboxylate 
• 500548-53-8 tert-butyl (2S)-5-bromo-2-{[methoxy(methyl)-amino]carbonyl}indoline-1-carboxylate 
• 500548-52-7 1-tert-butyl 2-methyl (2S)-5-bromoindoline-1,2-dicarboxylate 
• 141410-06-2 (S)-indoline-2-carboxylic acid methyl ester 
• 79815-20-6 (S)-indoline-2-carboxylic acid 
• 197460-36-9 methyl (S)-N-(tert-butoxycarbonyl)indoline-2-carboxylate 

Downstream Products

• 849480-33-7 (R)-2-((S)-5-Bromo-2,3-dihydro-1H-indol-2-yl)-1-methoxy-4-phenyl-butan-2-ol 
• 849480-34-8 (1R,9aS)-7-bromo-1-(methoxymethyl)-3,3-dimethyl-1-(2-phenylethyl)-9,9a-dihydro-1H-[1,3]oxazolo[3,4-a]indole 
• 849480-36-0 (1R,9aS)-1-(methoxymethyl)-3,3-dimethyl-1-(2-phenyl)ethyl-9,9a-dihydro-1H-[1,3]oxazolo[3,4-a]indole-7-carboxylic acid methyl ester 
• 849480-35-9 (1R,9aS)-1-(methoxymethyl)-3,3-dimethyl-1-(2-phenylethyl)-9,9a-dihydro-1H-[1,3]oxazolo[3,4-a]indole-7-carboxylic acid 
• 586390-98-9 (2S)-2-[(1R)-1-hydroxy-1-(methoxymethyl)-3-phenylpropyl]-2,3-dihydro-1H-indole-5-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Stereospecific synthesis of 2,2,3-trisubstituted tetrahydroquinolines: Application to the total syntheses of benzastatin E and natural virantmycin

An efficient methodology for the synthesis of 2,2,3-trisubstituted tetrahydroquinolines has been developed, which involves the triphenylphosphine- CCl4-mediated stereospecific rearrangement of α,α- disubstituted indoline-2-methanols 15 to 2,2,3-trisubstituted tetrahydroquinolines 26. The rearrangement precursors 15 are readily prepared by the diastereoselective Grignard addition to 2-acylindolines 13. The total syntheses of (+)-benzastatin E (1) and natural virantmycin (2a) were accomplished utilizing this methodology. This rearrangement reaction might afford some chemical precedent for the biogenetic pathway of the benzastatin family.

Total synthesis of (+)-benzastatin E via diastereoselective Grignard addition to 2-acylindoline.

[reaction: see text] A stereoselective total synthesis of (+)-benzastatin E (1) is described. The synthesis involves a diastereoselective Grignard addition to 2-acylindoline 2, which is derived from commercially available (S)-2-indolinecarboxylic acid (3). The unknown absolute configuration of (+)-1 is determined as (9S,10R).