356519-70-5

Upstream product

• 100-51-6 benzyl alcohol 
• 356519-68-1 (3R,3aS,6S,6aR)-3-[6-(1,3-benzodioxol-5-yl)hexyl]-2,2-bis(1,1-dimethylethyl)tetrahydro-6-methylfuro[3,4-d]-1,2-oxasilol-4(2H)-one 
• 93826-98-3 7-Benzo[1,3]dioxol-5-yl-heptanal 
• 356519-62-5 4-(7-octynyl)-1,2-(methylenedioxy)benzene 
• 356519-73-8 5-(8,8-dibromo-7-octenyl)-1,3-benzodioxole 
• 356519-64-7 (5R,6S)-5-[8-(1,3-benzodioxol-5-yl)-1-octynyl]-3-(1,1-dimethylethyl)-8,8-diethyl-2,2,6-trimethyl-4,7-dioxa-3,8-disiladecane 
• 356519-67-0 selenocarbonic acid O-(10-benzo[1,3]dioxol-5-yl-2-di-tert-butyl-silanyloxy-1-methyl-dec-3-ynyl) ester Se-phenyl ester 
• 356519-66-9 Imidazole-1-carboxylic acid (1S,2R)-10-benzo[1,3]dioxol-5-yl-2-di-tert-butyl-silanyloxy-1-methyl-dec-3-ynyl ester 
• 356519-65-8 (2S,3R)-11-(1,3-benzodioxol-5-yl)-3-[[bis(1,1-dimethylethyl)silyl]oxy]-4-undecyn-2-ol 
• 356519-63-6 (2S,3R)-11-(1,3-benzodioxol-5-yl)-2-[(triethylsilyl)oxy]-4-undecyn-3-ol 

Relevant academic research and scientific papers

Synthesis of (+)-juruenolide C: Use of sequential 5-exo-digonal radical cyclization, 1,5-intramolecular hydrogen transfer, and 5-endo-trigonal cyclization

Acetylenic alcohol 10 was converted successively into silane 11 and phenylseleno carbonate 14. On treatment with Ph3SnH, the latter underwent 5-exo-digonal radical cyclization, intramolecular hydrogen transfer, and 5-endo-trigonal cyclization, yielding 15. Conversion of the lactone into the lactol benzyl ether 17, carbon-silicon bond cleavage, and regeneration of the lactone carbonyl gave (+)-juruenolide C (1).