548757-15-9

Upstream product

• 548757-03-5 tert-butyl(diphenyl)silyl (3R,4R,5R,11S)-2-tert-butyl(diphenyl)silyloxy-1,4:3,5-diepoxy-1,2-secoeudesman-13-oate 

Downstream Products

• 548757-16-0 (S)-2-[(2R,2aR,4aS,7R,8aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-2a,4a-dimethyl-octahydro-1,3-dioxa-cyclobuta[c]inden-7-yl]-propionic acid 2-thioxo-2H-pyridin-1-yl ester 
• 548757-04-6 (3R,4R,5R,11S)-2-tert-butyl(diphenyl)silyloxy-1,4:3,5-diepoxy-1,2-secoeudesman-13-oic acid 
• 548757-18-2 (S)-2-[(2R,2aR,4aS,7R,8aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-2a,4a-dimethyl-octahydro-1,3-dioxa-cyclobuta[c]inden-7-yl]-propionyl chloride 
• 548757-06-8 (3R,4R,5R)-2-tert-butyl(diphenyl)silyloxy-1,4:3,5-diepoxy-1,2-secoeudesman-11-ol 
• 548757-05-7 (3R,4R,5R)-2-tert-butyl(diphenyl)silyloxy-1,4:3,5-diepoxy-1,2-seco-12-noreudesman-11-one 
• 548757-17-1 1-[(2R,2aR,4aS,7R,8aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-2a,4a-dimethyl-octahydro-1,3-dioxa-cyclobuta[c]inden-7-yl]-ethanol 
• 548757-12-6 (3S,4S,5R)-1,4:2,5-diepoxy-3-phenylselanyl-1,2-secoeudesman-11-yl acetate 
• 548757-11-5 (3S,4S,5R)-1,4:2,5-diepoxy-3-phenylselanyl-1,2-secoeudesman-11-ol 
• 548757-10-4 (3R,4R,5R)-1,4:3,5-diepoxy-2-phenylselanyl-1,2-secoeudesman-11-ol 
• 37209-50-0 (4R,5R)-1,4:2,5-diepoxy-1,2-secoeudesm-2-en-11-yl acetate 
• 548757-03-5 tert-butyl(diphenyl)silyl (3R,4R,5R,11S)-2-tert-butyl(diphenyl)silyloxy-1,4:3,5-diepoxy-1,2-secoeudesman-13-oate 

Relevant academic research and scientific papers

Synthesis of phytuberin. 4-endo-tet acid-catalyzed cyclization of α-hydroxy epoxides

The total synthesis of phytuberin, a phytoalexin of the Solanum genus, from (-)-α-santonin is reported. The key steps include (a) reductive cleavage of the C-O bond of the γ-lactone with concomitant protection of the C1 double bond, (b) Sharpless stereocontrolled hydroxy-assisted epoxidation of allylic alcohol 6 and simultaneous deprotection of the C1 double bond, (c) a rare 4-endo-tet acid-catalyzed cyclization of an α-hydroxy epoxide, and (d) an unprecedented 4-exo selenocyclization of a homoallylic alcohol.