960004-39-1

Upstream product

• 186581-53-3 diazomethane 
• 98-59-9 p-toluenesulfonyl chloride 
• 10396-97-1 4-methyl-N-((S)-2-oxotetrahydrofuran-3-yl)benzenesulfonamide 
• 1190409-86-9 methyl (2S)-2-[[(4-methylphenyl)sulfonyl]amino]-4-iodo-butanoate 
• 1666-13-3 diphenyl diselenide 

Downstream Products

• 960004-28-8 N-[(1S)-1-(hydroxymethyl)-3-(phenylseleno)propyl]-4-methylbenzenesulfonamide 
• 1190409-87-0 methyl (2S)-2-[[(4-methylphenyl)sulfonyl]-(2-butyn-1-yl)-amino]-4-(phenylseleno)butanoate 
• 1259286-19-5 (2S,3S,4E)-1-[(4-methylphenyl)sulfonyl]-4-[1-(benzyldimethylsilyl)ethylidene]-2-methoxycarbonyl-3-pyrrolidineacetaldehyde 
• 1259286-29-7 C₂₆H₃₃NO₆SSi 
• 1259286-22-0 methyl (2S,3S,4E)-1-[(4-methylphenyl)sulfonyl]-4-[1-(benzyldimethylsilyl)ethylidene]-2-methoxycarbonyl-3-pyrrolidineacetate 
• 1190409-95-0 (2S,3S,4E)-1-(4-methylphenylsulfonyl)-2-carboxy-4-[(2E,5R)-5-carboxy-1-methyl-2-hexen-1-ylidene]-3-pyrrolidineacetic acid 
• 1190409-94-9 methyl (2S,3S,4E)-1-(4-methylphenylsulfonyl)-2-methoxycarbonyl-4-[(2E,5R)-5-methoxycarbonyl-1-methyl-2-hexen-1-ylidene]-3-pyrrolidineacetate 
• 1190409-82-5 methyl (2S,3S,4E)-1-[(4-methylphenyl)sulfonyl]-2-(methoxycarbonyl)-4-(1-iodoethylidene)-3-pyrrolidineacetate 
• 1190409-97-2 (2S,3S,4E)-1-[(4-methylphenyl)sulfonyl]-2-(methoxycarbonyl)-4-(1-iodoethylidene)-3-pyrrolidineacetic acid 
• 1190409-93-8 methyl (2S,3S,4E)-1-[4-(methylphenyl)sulfonyl]-3-(2-hydroxyethyl)-4-(1-iodoethylidene)-2-pyrrolidinecarboxylate 
• 1190409-92-7 methyl (2S,3S,4E)-1-[4-(methylphenyl)sulfonyl]-3-[2-(tris(1-methylethyl)silyloxy)ethyl]-4-[1-(dimethyl(phenyl)silyl)ethylidene]-2-pyrrolidinecarboxylate 
• 1190409-91-6 (2S,3S,4Z)-1-(4-methylphenylsulfonyl)-2-carboxy-4-[(2E,5R)-5-carboxy-1-methyl-2-hexen-1-ylidene]-3-pyrrolidineacetic acid 
• 1190409-90-5 methyl (2S,3S,4Z)-1-(4-methylphenylsulfonyl)-2-methoxycarbonyl-4-[(2E,5R)-5-methoxycarbonyl-1-methyl-2-hexen-1-ylidene]-3-pyrrolidineacetate 
• 1190409-83-6 methyl (2S,3S,4Z)-1-[(4-methylphenyl)sulfonyl]-2-methoxycarbonyl-4-[1-(iodo)ethylidene]-3-pyrrolidineacetate 

Relevant academic research and scientific papers

Stereocontrolled total syntheses of isodomoic acids G and H via a unified strategy

Marine neuroexcitatory compounds isodomoic acids G and H were efficiently synthesized from a common intermediate using a silicon-based cross-coupling reaction. Dividing each target compound into the core fragment and the side-chain fragment enabled the synthesis to be convergent. The trans-2,3-disubstituted pyrrolidine core fragment was accessed through a diastereoselective rhodium-catalyzed carbonylative silylcarbocyclization reaction of a vinylglycine-derived 1,6-enyne. A stereochemically divergent desilylative iodination reaction was developed to convert the cyclization product to both E- and Z-alkenyl iodides, which would eventually lead to isodomoic acid G and isodomoic acid H, respectively. The late-stage alkenyl-alkenyl silicon-based cross-coupling reaction uniting the core alkenyl iodides and the side-chain alkenylsilanol was achieved under mild conditions. Finally, two mild deprotections afforded the target molecules.

Total syntheses of isodomoic acids G and H

(Chemical Equation Presented) The total syntheses of marine natural products belonging to the kainoid family, isodomoic acids G and H, are described. The strategic connection involves a sequential silylcarbocyclization/ silicon-based cross-coupling proces

Stereocontrolled synthesis of substituted N-arenesulfonyl azetidines from γ-(phenylseleno)alkyl arylsulfonamides

Different synthetic methodologies for the stereocontrolled synthesis of substituted azetidines are reported. The approach utilizes an optimized oxidation reaction of γ-(phenylseleno)alkyl arylsulfonamides, followed by the intramolecular substitution of th