Tandem Wittig-ene reaction approach to kainic acid.
The first example of a tandem Wittig-intramolecular ene reaction approach and its application toward the synthesis of kainic acid is reported. The synthetic pathway involves conversion of prenyl bromide into phosphorane 3, followed by one-pot Wittig olefination and an ene reaction with glyoxalic acid to give the cis fused pyrrolidine skeleton of kainic acid.
Department of Chemistry, Goa University, Taleigao Plateau, Goa 403 206, India.
Mahesh S
MS
Majik
Peruninakulath S
PS
Parameswaran
Santosh G
SG
Tilve
D007608:Kainic Acid / Q000138:chemical synthesis*; D011760:Pyrrolidinones / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D011760:Pyrrolidinones; D007608:Kainic Acid