90605-98-4

Upstream product

• 71392-28-4 (3S,4S,5R)-3-amino-4,5-dimethyldihydrofuran-2(3H)-one 
• 105708-56-3 (-)-funebral 
• 674785-82-1 (3S,4S,5R)-3-[2,5-Bis-(2-methyl-propenyl)-pyrrol-1-yl]-4,5-dimethyl-dihydro-furan-2-one 
• 674785-83-2 1-((3S,4S,5R)-4,5-Dimethyl-2-oxo-tetrahydro-furan-3-yl)-1H-pyrrole-2,5-dicarbaldehyde 

Relevant academic research and scientific papers

Syntheses of (-)-Funebrine and (-)-Funebral, Using Sequential Transesterification and Intramolecular Cycloaddition of a Chiral Nitrone

The first syntheses of (-)-funebrine [(-)-1] and (-)-funebral [(-)-2] are described. The syntheses feature sequential formation of nitrone VI from methyl glyoxylate (5) with oxime 6, transesterification of nitrone VI with (E)-crotyl alcohol (4), and intramolecular cycloaddition of the resulting nitrone VII bearing crotyl ester to afford cycloadduct 7 as a major product. The adduct 7 was readily elaborated to amino lactone (-)-3, the key synthetic intermediate of (-)-1 and (-)-2.