165605-86-7

Upstream product

• 152442-10-9 (4R,5R)-4,5-dihydro-4-hydroxy-5-iodomethyl-2(3H)-furanone 
• 4832-52-4 tris(phenylthio)methane 
• 1025911-12-9 (4S,5R)-5-Tridecyl-4-(tris-phenylsulfanyl-methyl)-dihydro-furan-2-one 
• 74-88-4 methyl iodide 
• 897657-63-5 (4R,5R)-4-Hydroxy-5-tridecyl-4,5-dihydro-2(3H)-furanone 
• 76291-91-3 (R)-5-tridecyl-5H-furan-2-one 
• 15890-72-9 laurylmagnesium bromide 

Downstream Products

• 19464-85-8 (+)-roccellaric acid 

Relevant academic research and scientific papers

Concise syntheses of natural γ-butyrolactones, (+)-trans-whisky lactone, (+)-trans-cognac lactone, (-)-methylenolactocin, (+)-nephrosteranic acid, and (+)-roccellaric acid using novel chiral butenolide synthons

cis-4-Hydroxy-5-(iodomethyl)-4,5-dihydro-2(3H)-furanones (1 and ent-1) were converted by cross-coupling with several Grignard-derived cuprates followed by benzoylation and base-induced elimination into new chiral butenolides 12, 14, ent-14, 20, and 27. The sequential conjugate addition - quenching of these butenolides under complete stereocontrol provided several polysubstituted γ-butyrolactones including flavor components [(±)-trans-whisky lactone (3) and (+)-trans-cognac lactone (4)], the antitumor antibiotic lactone (-)-methylenolactocin (5), and lichen components [(+)-nephrosteranic acid (7) and (+)-roccellaric acid (8)].