157497-28-4

Upstream product

• 151379-77-0 (R)-N-Benzyl-N-methyl-3-hydroxy-4-pentenamide 
• 157497-24-0 (4R,5R)-4-Hydroxy-5-undecyl-4,5-dihydro-2(3H)-furanone 
• 157497-27-3 (5R)-5-undecyl-2,5-dihydro-2-furanone 
• 152442-10-9 (4R,5R)-4,5-dihydro-4-hydroxy-5-iodomethyl-2(3H)-furanone 
• 17049-50-2 n-decyl magnesium bromide 
• 4832-52-4 tris(phenylthio)methane 
• 74-88-4 methyl iodide 
• 14572-78-2 lithium tris(phenylthio)methanide 

Downstream Products

• 70579-56-5 (2R,3S,4S)-(+)-2-undecyl-4-methyl-5-oxo-tetrahydrofuran-3-carboxylic 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)].

New Entry to Chiral Butenolide Synthons. Application to Expeditious Syntheses of (+)-Nephrosteranic Acid, (+)-trans-Whisky Lactone, and (+)-trans-Cognac Lactone

A new entry to chiral butenolide synthons starting with iodolactonization of the readily available, homochiral N-benzyl-N-methyl-3-hydroxy-4-pentenamide (1) and its application to the syntheses of (+)-nephrosteranic acid (5), (+)-trans-whisky lactone (6), and (+)-trans-cognac lactone (7) are described.