956219-55-9

Upstream product

• 79-22-1 methyl chloroformate 
• 338463-00-6 N-(tert-butoxycarbonyl)-N-but-3-ynyl-4-methylbenzenesulfonamide 
• 18303-04-3 N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide 

Downstream Products

• 217175-26-3 C₅₅H₇₀N₂O₁₂SSi 
• 217175-27-4 C₅₅H₇₂N₂O₁₁SSi 
• 217175-22-9 C₄₇H₅₈N₂O₁₀SSi 
• 217175-25-2 (2S,3S,4R)-2-[(R)-1-Benzoyloxy-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-(2-methyl-allyl)-5-oxo-3-[2-(toluene-4-sulfonylamino)-ethyl]-pyrrolidine-2-carboxylic acid ethyl ester 
• 217175-24-1 (4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-[(3R,4S)-3-(2-methyl-allyl)-2-oxo-1-(toluene-4-sulfonyl)-piperidin-4-yl]-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid ethyl ester 
• 217175-34-3 (4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-[(S)-1-methoxycarbonylmethyl-3-(toluene-4-sulfonylamino)-propyl]-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid ethyl ester 
• 217175-23-0 (4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-[(S)-2-oxo-1-(toluene-4-sulfonyl)-piperidin-4-yl]-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid ethyl ester 
• 956219-58-2 C₃₀H₄₆N₂O₆SSi 
• 217175-28-5 (3R,4S,5S,9R)-9-Hydroxy-3-(2-methyl-allyl)-6-oxo-4-[2-(toluene-4-sulfonylamino)-ethyl]-7-oxa-1-aza-spiro[4.4]nonane-1-carboxylic acid tert-butyl ester 
• 217175-29-6 (3R,3aS,6aS,9R,9aS)-9-Hydroxy-3-(2-methyl-allyl)-6-(toluene-4-sulfonyl)-octahydro-7-oxa-1,6-diaza-cyclopenta[d]indene-1-carboxylic acid tert-butyl ester 
• 956219-57-1 C₂₁H₂₆N₂O₅S 
• 217175-21-8 C₁₈H₂₅NO₆S 

Relevant academic research and scientific papers

Total synthesis of (-)-sarain A

This article describes the details of our synthetic studies toward the complex marine alkaloid sarain A. Various strategies were conceived, setbacks encountered, and solutions developed, ultimately leading to a successful enantioselective total synthesis. Our route to (-)-sarain A features a number of key steps, including an asymmetric Michael addition to install the C4′-C3′-C7′ stereotriad, an enoxysilane-N-sulfonyliminium ion cyclization to set the C3 quaternary carbon stereocenter, and assemble the diazatricycloundecane core, a ring-closing metathesis to construct the 13-membered ring, an intramolecular Stille coupling to fashion the unsaturated 14-membered macrocycle, and a late-stage installation of the tertiary amine-aldehyde proximity interaction.