Synthesis of substituted 3-furanoates from MBH-acetates of acetylenic aldehydes via tandem isomerization-deacetylation-cycloisomerization: access to Elliott's alcohol.
A new method for the synthesis of 5-substituted furan-3-carboxylates from Morita-Baylis-Hillman acetates of acetylenic aldehydes is reported. The process involves palladium-catalyzed isomerization followed by base-promoted deacetylation and cycloisomerization reactions. The utility of this chemistry is further demonstrated by the synthesis of Elliott's alcohol, a key intermediate of the pyrethroid resmethrins.
Division of Natural Products Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad - 500607, India. rajireddy@iict.res.in.
Chada Raji
CR
Reddy
Gaddam
G
Krishna
Motatipally Damoder
MD
Reddy
D000085:Acetates / Q000737:chemistry*; D000107:Acetylation; D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000085:Acetates; D000438:Alcohols; D000447:Aldehydes; D002264:Carboxylic Acids; D005663:Furans