545362-99-0

Upstream product

• 55149-84-3 2-nitroveratraldehyde 
• 545363-22-2 (3S)-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-hydroxymethyl-pent-4-ynoic acid ethyl ester 
• 634912-25-7 2-(2-iodo-6,7-dimethoxy-1H-indol-3-yl)-ethanol 
• 545362-91-2 3-(3,4-dimethoxy-2-nitro-phenyl)-acrylic acid ethyl ester 
• 545363-24-4 3-(2-formylamino-3,4-dimethoxy-phenyl)-acrylic acid ethyl ester 
• 545362-93-4 3-(3,4-dimethoxy-2-isocyano-phenyl)-acrylic acid ethyl ester 
• 545362-97-8 acetic acid 2-(2-iodo-6,7-dimethoxy-1H-indole030yl)-ethyl ester 
• 545362-88-7 (3S)-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-dimethoxymethyl-pent-4-ynoic acid ethyl ester 

Downstream Products

• 545363-26-6 (3'S)-3-(2-acetoxy-ethyl)-2-[6'-(tert-butyldiphenyl-silanyloxy)-3'-dimethoxymethyl-3'-ethoxycarbonylmethyl-hex-1'-ynyl]-6,7-dimethoxyindole-1-carboxylic acid tert-butyl ester 
• 545363-32-4 (11S)-(12Z)-11-ethoxycarbonylmethyl-11-formyl-1,2-dimethoxy-7-(2-nitro-benzenesulfonyl)-6,7,8,9,10,11-hexahydro-5H-7,14-diaza-cycloundeca[a]indene-14-carboxylic acid tert-butyl ester 
• 545363-06-2 (11S)-(12Z)-11-dimethoxymethyl-11-ethoxycarbonylmethyl-1,2-dimethoxy-7-(2-nitro-benzenesulfonyl)-6,7,8,9,10,11-hexahydro-5H-7,14-diaza-cycloundeca[a]indene-14-carboxylic acid tert-butyl ester 
• 545363-04-0 (1'Z)-(3'S)-2-(3'-dimethoxymethyl-3'-ethoxycarbonylmethyl-6'-hydroxy-hex-1'-enyl)-6,7-dimethoxy-3-[2-(2-nitro-benzenesulfonylamino)-ethyl]-indole-1-carboxylic acid tert-butyl ester 
• 545363-28-8 (1'Z)-(3'S)-2-[6'-(tert-butyldiphenyl-silanyloxy)-3'-dimethoxymethyl-3'-ethoxycarbonylmethyl-hex-1'-enyl]-3-(2-hydroxy-ethyl)-6,7-dimethoxy-indole-1-carboxylic acid tert-butyl ester 
• 545363-02-8 (1'Z)-(3'S)-3-(2-acetoxy-ethyl)-2-[6'-(tert-butyldiphenyl-silanyloxy)-3'-dimethoxymethyl-3'-ethoxycarbonylmethyl-hex-1'-enyl]-6,7-dimethoxyindole-1-carboxylic acid tert-butyl ester 
• 545363-30-2 (1'Z)-(3'S)-2-[6'-(tert-butyldiphenyl-silanyloxy)-3'-dimethoxymethyl-3'-ethoxycarbonylmethyl-hex-1'-enyl]-6,7-dimethoxy-3-[2-(2-nitro-benzenesulfonylamino)-ethyl]-indole-1-carboxylic acid tert-butyl ester 
• 634911-98-1 ((3aR,10bS,12bS)-7,8-Dimethoxy-4-phenylsulfanyl-2,3,4,5,11,12-hexahydro-1H-6,12a-diaza-indeno[7,1-cd]fluoren-3a-yl)-acetic acid ethyl ester 
• 634911-97-0 3-(2-Acetoxy-ethyl)-2-[(Z)-(S)-3-dimethoxymethyl-3-ethoxycarbonylmethyl-6-(2-nitro-benzenesulfonylamino)-hex-1-enyl]-6,7-dimethoxy-indole-1-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Enantioselective total synthesis of aspidophytine

(Matrix presented) An enantioselective total synthesis of aspidophytine is described. The indole fragment bearing a cis-alkene substituent was efficiently prepared through radical cyclization of a 2-alkenylphenylisocyanide followed by Sonogashira coupling of the generated 2-iodoindole derivative with a functionalized acetylene unit. After formation of the 11-membered cyclic amine, the aspidosperma skeleton and lactone ring were constructed to complete the total synthesis.

Stereocontrolled total synthesis of (-)-aspidophytine

The enantioselective stereocontrolled total synthesis of aspidophytine is described. The key indole intermediate was prepared by radical cyclization of 2-alkenylphenylisocyanide, followed by Sonogashira-coupling with a highly functionalized terminal acetylene. The 11-membered cyclic amine, a precursor for the formation of the aspidosperma skeleton, was synthesized using nitrobenzenesulfonamide chemistry. After construction of the pentacyclic skeleton, the lactone ring was formed to complete the total synthesis.