606146-01-4

Upstream product

• 10113-39-0 N-formyl-2-iodoaniline 
• 107-19-7 propargyl alcohol 

Downstream Products

• 221903-27-1 3-{2-[(4-dimethoxymethyl-hexyl)-(2,4-dinitro-benzenesulfonyl)-amino]-ethyl}-2-(1-methoxycarbonyl-vinyl)-indole-1-carboxylic acid tert-butyl ester 
• 221903-33-9 3-{2-[(2,4-dinitro-benzenesulfonyl)-(4-ethyl-2,3-dihydro-furan-2-ylmethyl)-amino]-ethyl}-2-(1-methoxycarbonyl-vinyl)-indole-1-carboxylic acid tert-butyl ester 
• 221903-34-0 2-(3-{2-[(2,4-dinitro-benzenesulfonyl)-(4-ethyl-5-hydroxy-tetrahydro-furan-2-ylmethyl)-amino]-ethyl}-1H-indol-2-yl)-acrylic acid methyl ester 
• 221903-28-2 2-(3-{2-[(2,4-dinitro-benzenesulfonyl)-(4-formyl-hexyl)-amino]-ethyl}-1H-indol-2-yl)-acrylic acid methyl ester 
• 221903-20-4 Acetic acid (Z)-3-(2-formylamino-phenyl)-allyl ester 
• 221903-21-5 Acetic acid (Z)-3-(2-isocyano-phenyl)-allyl ester 
• 606146-03-6 2-(3-chloro-1-propynyl)formanilide 
• 90097-52-2 2-chloro-3-(chloropmethyl)quinoline 
• 606146-02-5 methanesulfonic acid 3-(2-formylamino-phenyl)-prop-2-ynyl ester 
• 221903-19-1 acetic acid 3-(2-formylamino-phenyl)-prop-2-ynyl ester 

Relevant academic research and scientific papers

Biradicals/zwitterions from enallene-isonitriles. Formal [4 + 1] cycloadditions leading to 11H-indeno[1,2-b]quinoline and related compounds

1,3-Prototropic rearrangement of the benzannulated enyne-isonitriles to the corresponding enallene-isonitriles followed by cycloaromatization generated the putative quinoline biradicals/zwitterions. A subsequent intramolecular radical-radical coupling or electrophilic aromatic substitution then gave the formal [4 + 1] cycloaddition adducts leading to 11H-indeno[1,2-b]quinoline and related compounds.

Efficient total syntheses of (±)-vincadifformine and (-)-tabersonine

Stereocontrolled biomimetic total syntheses of the title compounds are described. Our syntheses feature a highly efficient preparation of the key intermediate 11 using our novel indole synthesis methodology. A novel amine protecting protocol by means of 2,4-dinitrobenzenesulfonamides has been developed to ensure the formation of the elusive secodine (3) as well as secodine-type intermediate (4) under very mild conditions.